Gossip Fox
by Vermilion Pendulm
Summary: How will the upperside of Ny handle the crazyness that is Naruto as he is reborn into a new world and he has to fit in this new world or has he already done that. xoxo Gossip Girl
1. Chapter 1

I **do not own the rights to either Naruto or Gossip Girl**

 **Chapter 1**

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Naruto Uzumaki was someone of virtue but that all changed when Sasuke had killed them in their final fight, but the god taken pity on him and decided to give him a new life. The thing was that Naruto was reborn and kept his name but his parents who were rich were killed in a gun incident which left Naruto as an orphan again. Fate has had a cruel part to him but he was taken up by nice people who then became his foster parents.

 **Manhattan New** **York**

2004

An young 6 year old, Naruto was looking around in the hopes of liking where he was as he watched his foster parents were talking to get a place in the Manhattan area. As his parents were busy he noticed a little blond girl drop a little doll that was in her hand. So being the good person that he was he picked up the doll and flash a cheesy grin to the said girl and pick up the doll. "Um here's your doll and hi im Naruto Fox." The red head extended his hand to the girl seeing the shook on her face.

"Um-mm you dont know who i am." The red head only shake his head and the blond-net could only smile at his response. "Well I'm Serena Van Der Woodsen, will you be my friend i don't have many good ones in here." The red head could only smile and nod his head saying yes to her and from that moment started a great deal of craziness and drama but we will get to that later.

"Serena where are you? It was her time to go Serena was sad but Naruto only smiled at her and promised that they could play with each other later. Serena gave Naruto a hug and took her doll from his hand and left to her mother who was looking at the said red head when her daughter was going to her. Naruto could only sigh maybe living in this town wouldn't be so bad.

 **A few years** **later**

Right now Naruto was just relaxing as he was trying to get out of bed but a net of blond hair was in his way which cause him to only smirk. It was Serena she was cuddling up on him now this was something she always did even when they were kids. They even went out a few times but it didn't last when Serena's dad had left them she was broken and was looking for attention. It only got worse when he saw that Serena's younger brother Eric was trying to take his life but Naruto had stop him and with his help he had gotten the help he needed. Now Naruto at the time didn't know the important of the Van der Woodsen name but when he did it didn't change his opinion of Serena to which she loved about him. Then there was Lily, Serena's mother she was an attractive older blonde,Naruto couldn't lie.

Lilly was many things but she was is the daughter of music executive producer Rick Rhodes and Celia Rhodes. She later attended Brown University before marrying William van der Woodsen and moving into a penthouse on the Upper East Side. Before her marriage, she dated Rufus Humphrey and gave birth to their love child, whom she gave up for adoption. To which she had told Naruto in confidence. Lily is a very proud and refined woman. Being an extremely rich New Yorker since birth, she is a socialite and lives off the money from the settlements of her many divorces and her own family inheritance. Lily cares a lot about maintaining her social status and her family image. To which made Naruto stop being around her because of that type of attitude.

Over the years Serena had another best friend named Blair Waldorf. Who Naruto didn't really to much like a lot but he ,only accepted her for Serena's is the daughter of Harold and Eleanor Waldorf, respectively a successful lawyer and fashion designer. Her parents divorced after her father was caught cheating on Eleanor with another man named Giles, which caused Eleanor to divorce him. Blair father Harold soon moved to France with Giles, leaving Eleanor and Blair on the Upper East Side. Blair grew up being best friends with Serena Van der Woodsen and Nate Archibald and sometimes Naruto.

Even with the loss of her dad that left her and her brother seeing a doctor. It seemed like Serena was out of control. She did things like first break up with Naruto and seeing guy to guy. Off course Naruto didn't take it personal but always keep his eyes out for her when ever she crashed and burned. Then another thing she did was drinking and by god was she a bit of an addict. Naruto didn't want to be a jerk to his ex, but only made sure she was always getting home safe and made sure guys at clubs would not decided to do something their not suppose to.

* * *

It was then as the red head was relaxing at his place when he heard a knock at his door he went to his door and opened it to see Serena and she seemed very upset. Naruto was rubbing his eyes and look at his friend, " Serena whats wrong." The red head had said as he tried to comfort his friend, but she was moving and pacing around to much. She looked at her friend with a tear face as could only weep more. " It's bad Naru, its really bad i think i really went out of control now and i spoke to my mom and i will be going to a board school." She stated with more tears coming from her eyes.

Naruto could only look shocked at his blond friend and could only hug his friend as she continued crying he decided to help with her stuff and not even question her. As she was his friend and he could never truly judge her the only problem would be that Blair would wonder where her best friend is. That wasn't truly his problem anymore as he took the ride with Serena's mom and her as they went to the train station going to Cornwall, Connecticut. Lily left leaving only Naruto and Serena to themselves before the train would arrive. Serena was staring into the red head grey eyes as they continued to hug before she had left a kiss on his cheek as the train had then arrived to the stop. Naruto could only look at his blond female friend and could only utter one word as she got on the the train. "Tough melons!" The red head had muttered under his breath as he waved to his friend as she got on the train.

Naruto could only sigh as he looked at Lilly who didn't look to happy about it but they both got in the car as the ride was a quiet one, as she had dropped off Naruto could only think and wonder what was so bad that Serena had to leave Manhattan. The red head could only wonder but thought it was nothing. Little did Naruto know but this was a whole cause and effect of many things that will start in the upper side of Manhattan.

The next morning Naruto headed to school seeing Blair with her cronies as it seemed she was looking for Serena. The other thing was that Nate, Blair's new boyfriend was looking very guilty about something but the red head didn't know what. Then there was Chuck Bass a rich asshole who had a lot of money and pretty much a creep some of the Chuck had this curse of being incredibly handsome in a men's aftershave commercial kind of way. Women, and even a few men, can hardly resist him. He has dark brown hair and dark chocolate eyes. His hair is always perfectly styled, his skin has a natural tan, and he is always well dressed, often wearing stylish, colorful, well-tailored suits. Chuck is acknowledged as a fashion icon for men's wear, and is known for wearing a lot of purple in his outfits. Throughout the first season, he's known for wearing a printed scarf everywhere Chuck is very sleazy, self centered, and has a horny sense of humor. However, he is also shown to be very loyal to the select few he deems worthy, such as offering a loan for Nate and Anne Archibald for some reason.

Naruto was walking to class as he was stopped by as he saw the brunet was looking annoyed and angry. " Naruto where is Serena, i been trying to call her the whole time and she not answering? She asked questioningly as she looked at the red head tapping her knee high heels impatiently looking for the answer from him. Naruto could only look at the brunette with an upset look. "She gone Blair she left to go some boarding school and she seemed very scared about something." The red head stated as everyone eyes where on him especially Nate who looked very upset about it.

Nathaniel "Nate" Archibald is a lacrosse player at the elite St. Jude's School for Boys. His mother, Mrs. Archibald, is a French socialite, and his father, Captain Archibald, is a former Navy captain and a wealthy banker. Nate's best friends are Blair Waldorf and Serena van der Woodsen. Nate's family resides in a gracious townhouse right off Park Avenue on the exclusive Upper East Side of Manhattan in New York City, and his mother's French socialite family owns a summer chateau in Nice. He is a fan of sailing like his father, and wished to do that instead of attending Yale with his girlfriend Blair, although he expressed interest in attending Brown is a very warm and trusting person. He is kind and caring, especially to his closest friends. He is charming, laid-back, funny, and friendly, and it has always been in his nature to look out for people. Nate is also known for having a moral compass compared to all the other friends.

He is not comfortable with the privileges that his family's money and status give him because he thinks he does not deserve them and that they only control him. He is incredibly athletic and cares for his family deeply. Nate is also honest, and is known for being a horrible liar. Nate's negative trait might be that he is a bit hypersexualized, even getting involved with women who are much younger or older than he is but Naruto didn't mind that.

Naruto was in the bathroom as he saw his best friend had just entered." Naruto i have to tell you something important and its about Serena. Its about me and Serena." As Nate exclaimed looking at his friend and what Nate said will be one of the many things that have many blow the upper side of NY.

* * *

 **Another one more year later.**

 **Grand Central Station**

Serena walking in from the train station and a girl from a far watches and took the picture.

 **Gossip girl (voice ) "hey upper-siders Gossip Girl here, and i have some biggest news ever one of many sources melanie91 sent us this, spotted at this, spotted at grand central bags in Serena Van der Woodsen. Wasn't it only one year ago our "it" girl mysteriously disappeared for "boarding school"? And just as suddenly, She's back don't believe me? See for yourselves lucky us, melanie91 sent proof. Thanks for the proof for the photo, Mel.**

While on the same train side direction two young teenagers got of the train as older dark haired male was waiting patiently for his children as smiled and saw them. "Jenny, Dan over here the older male. As he was trying to get the attention of his he saw his children as they both ran up and hugged them both. The first one being very short (around 5'0), having curly brown blond hair was Jenny. " Jenny is tall and skinny, with blonde hair due to her being interested in fashion, her style is often chic and well put together.

"Hey dad!" She said as she hug her father and looking very uncomfortable.

Dan is clever, as he was basically the smartest in his class, and also witty and patient; he works hard for what he wants and normally achieves his goals

Rufus then looked at his daughter, and then asked "Hey, Hey! You made it. Welcome back!How was your weekend at your mother's and how is she. Both the children had given looks as they both gave out an answer. "She's fine./good.

"Fine i Guess." Jenny said annoyed as she gave out a sigh not wanting to continue the conversation as it was getting bothersome. She looks at her brother who as well didn't want to have the conversation. Dan then spoke up " she 's good and fine." He stated as he too was uncomfortable with the conversation as well. Rufus looked at both his kids not taken notice of the mood but only said this " like maybe i should of never left Manhattan , fine taking a time out of from the my marriage was the best idea i"ve ever had fine? The father of the two kids stated to the both of them.

"Dad you know im starving." Dan said as he tried to change the mood in the whole matter. It work as his dad bought it. "Yeah lets go home.I'm cooking Caprese salad with a little mozzarella di Bufala... yeah, i'm gonna make you guys... " As Rufus put his arm around his daughter and they walked off, Dan turns around and see Serena not believing that his crush is back but does she even remember him.

 **Gossip Girl voice over " Spotted: Lonely boy...cant believe the love of his life has returned. If only she knew who he was. But everyone knows Serena. and everyone is talking.**

* * *

As Serena was walking from the train station she saw a car coming up, and saw a red head young teen with three whiskers scars on his face and a fox that was on his shoulder. She ran up to him "Naru" she said excitingly and hugged her favorite male friend. Naruto looked back at her and hugged back " hey Serena welcome back so do you want to tell me why you took Nate's virginity and is that the reason why you left?" He asked questioningly looking at his friend with concern on his face. Serena looked back at her friend "look Naru it's one of the reason why i decided to leave." She stated to her red friend. Naruto looked back at his blonde friend and asked "then what was the main reason you decided to go?" He asked again she looked at him with tears in her eyes " it all started when i meet this girl named Georgina.

 **on the streets**

Several people are standing in the streets, looking at the newest Gossip Girl' entry on their cell phone

 **Gossip Girl:" Wonder what Blair Waldorf , they"re Bffs but we always thought Blair's boyfriend Nate had a thing for Serena.**

 **Mean while at the Waldorf suite**

A certain queen bee was reading the latest news from gossip girl "Serena back is back!" The queen bee exclaimed to herself not sounding to happy as she saw a text message and different pictures from people.

Blair leaves the bathroom to return to the party as she taken notice that her mother was talking to her friend. "I have to design a dress for this women." The women stated as she turned to her daughter taken notice of the dress she was wearing. "Blair, if you"re gonna wear one of my designs tell me about it so we can at least get it properly fitted."

Blair had just looked at her mother not really paying attention as the thoughts of her ex best-friend was on her mind."Thanks mom. I"ll keep that in mind great party." The queen bee had said as she was walking away with a small smile as she was now looking for her boyfriend in hopes to distract her from her she heading towards her boyfriend seeing that he was talking to a few party guest with his father. "So Nate started thinking about college?" One person in the party asking the young society rich kid. Nate's father was also intrigued as he then spoke " well actually I'm a Dartmouth Man." The man said but not taken notice of Nate's face at his father's answer and decided to challenge. "yes, dad's always spoken very highly of i would like to check out west. You know maybe Usc or Ucla?" Howie look back at his son challengelly and only had a brief laugh " his mother wouldn't hear it .Dartmouth is far enough for her. Nate look back at his father and only stated "yes well... Dartmouth is my first choice.

Blair walks up to her boyfriend and his father also called the captain as she was trying to get their attention. "Excuse me captain. Nate can i borrow you." Nate looked back at his dad who gave him a nod and looked at his girlfriend."Eh sure, excuse me for a second." The young man had said but not before he saw his best friend Chuck was sitting near two girls. So Nate sat down with Chuck as his friend was giving him a look. "Nathaniel, any interest in some fresh air." The rich play only hinting that he wanted to smoke with his friend. Nate looked back at his friend and sighed."When i get back? he said confusingly as his girlfriend came up and gave a glare to Chuck.

"If he gets back! The queen bee exclaimed as she then was leading her boyfriend upstairs and into her bedroom as she push him down onto her bed. Nate was looking at Blair very confused about what was going on."Whats going on? Nate said as he looked to his girlfriend not seeing her being a little hurt. She look back at him while also blush but not to much. "I wanna do this...it...now." The queen b said while also lying to her boyfriend in hopes to get Serena off her mind. Nate looked confused again "Now,now? You wanted to wait... What changed." he asked wanting to find out the answer. " Not any more" Blair stated as she tried to strip and kiss Nate.

 **Better lock it down, with Nate B, clock ticking**

Meanwhile downstairs

Chuck was playing with his drink looking bored waiting for his friend as two girls were reading a text message. "Oh my god Isabel, you''ll never believe whats on Gossip Girl." The girl said to her friend. " I know Katy someone saw Serena get off a train at Grand central." Both the girls continued talking about the ex "It girl"as Chuck could only give a creepy smirk. "Good, things were getting a little dull around here." The rich play boy stated as all the guest saw the said blond walk into party.

 **Back with Nate and Blair**

The queen bee was in a tongue wrestle with her boyfriend as both are undressed. " I love you Nate Archibald. Always have and will." The queen bee said with fake affection but did actually mean it. The young male brunette looked back at his girl and kissed her back." I love you too." he said with actual care in his voice. But little they both know that their world would soon crash down well at least for Blair.

Serena walks in and got noticed by Blair's mother Eleanor. The women had ran up to Serena and gave her a hug. "Serena Van de Woodsen? Is that you how are you? Blair is gonna be happy to see you let me go get her. The women left the blond as she went upstairs. " Blair, it's Serena she is here go say hi to her." The women said as she was knocking on the door. In the room Nate ears perk up when he heard that name. As he had stopped kissing his girlfriend."Serena? he asked back looking at girlfriend and also looking worried. "Serena is at school. Kiss me." she said trying to doge the question. Nate only looked at her as he raised his eyebrows. "No i think i heard your Mom say she's here. "Don't you wanna say hey?" Nate asked as he got of the bed and got dressed which disappointed the queen bee. Blair could only look the other way. "Yeah... totally." The young brunette said as she was truly upset about the matter.

 **Back-down stairs at the party**

Serena was walking through the party as the party guest started talking behind her back. "I heard she is pregnant ... rehab... she look good." Some of the party guest started to mumble to their-selves as they continued to talk among themselves. Serena ignored all the talk as she walk up and see her mother who was talking to a friend."So i told him forget;i don't care if it's mahogany. It clash my sofa." The older blond said jokingly. "Mom... Mom!... Hey" The older blond women had hugged her daughter."Oh,Serena darling." The older blond women said surprised as she has hugged her oldest child. Serena looked at her mother as she was looking around."So where is he?What they haven't let him out yet." The younger blond asked as he wondering where her brother was asking the mother the question. Lily looked back at her daughter as she could only scoff at the question from her daughter."Lets not discuss this right now ok? I thought you might want to see some of your friends." Lily said to her daughter trying to doge the question as she did not want to have the said conversation. To which this had confused and made Serena a little angry."Thanks" The younger blond said annoyed as she left, but she saw and took notice of Nate of the other side of the room.

Blair had opened her bedroom she walks to the room. As she tried to block Nate view from Serena as she ran up to her and they hugged each other. The queen bee looked very uncomfortable but she gave a smile to her ex-best-friend."Hi Serena so good to see you." The It girl didn't look to convinced from her best-friend looking happy to see her. Blair gave her friend another small smile. "come we"re about to have dinner will join us." The queen bee asked trying to hide her anger. Then Blair's mother also gave a smile to Serena." I"ll set a place for you at the table next to Blair." The older brunette asked the younger blond the question. Serena look back awkwardly to both Blair and Eleanor."yeah, actually there somewhere i have to go." Serena looked a little upset but at the same time she did not want to cause any tension between her and Blair. Blair just gave a look of shook towards her best friend. " Your leaving, but you just got here? The queen bee asked confused and even more angry at her friend that betrayed her. Serena could see the look on her face but she didn't want to add on to it. "Yeah i just wanted to say hi towards,besides i'm not feeling well. I just wanted to say hi. I"ll see you at school tomorrow. The blond "It girl" said to her friend as she gave one last final hug to Blair as she left the party.

Blair look back as she was still upset about the news with her best-friend. "School...so i guess she's back for good." The queen bee said as she was annoyed about the whole matter. As Katy walked up to queen bee with raised eyebrows at the girl. "Didn't you know she was coming?" The Asian black haired beauty asked . Blair looked back at her with a fake smile on her face.

"Off course i did.I just...wanted it to be a surprise. Both Katy and Isabel weren't really convinced by the queen bee demeanor but they decided to let it go as they saw her pacing around thinking about a certain blond.

 **Gossip Girl voice: Word is that S Bailed on B's party in under 90 seconds and didn't even have one lemon shot. Has our bad girl really gone good? Or is it just an act?**

Serena walks in as she has passed the nurse's station and looks into a patients room. The nurse took notice of Serena and was annoyed because it was time for the place to close."Young lady you can't be here, Vising hours are over."The nurse looked real annoyed but the young blond teenager was determined. Serena just gave a sad look to the nurse."I'm Family and he's my brother, i haven't seen him in over a long while." The "It girl" begged as she truly wanted to she her brother.

* * *

 **Somewhere else**

Naruto was walking downtown in the other side of Ny. As he rang the bell he got answered in. The person had opened the door and hugged Naruto as she had quickly gave him a passionate kiss. "well hello there stranger what are you doing on this side of town." The strange female said as she had continue to kiss the red head. Naruto could only smirk and give a kiss back. "well you know trying to cause a bit of chaos here and there. The red head stated to the female as they had continued kissing with lust and affection. The strange female looked at Naruto affectionately and had a little smirk on her face."So whats the plan on how to crash the inner society Foxy." The girl stated with a bit of mischief in her eyes. Naruto back at the girl could only smirk back at the girl as he look at her. "The plan has always been the same my dear which is to get rid of anyone who gets in my way because they would soon regret it. The girl could only grin her teeth as she looked back at Naruto. "enough talk foxy back to kissing and making out." Naruto could only smirk at her as he continued to do just that. " Yes mam as he pick up the girl and continued his action as he grip her ass.

 **It seems like everyone favorite cute fox knight is hiding something, does it have anything to do with Serena leaving to go to boarding school because word was that our favorite Fox cutie is not at all as he appears. XoXo Gossip Girl**

The next day Naruto decide to call a number as he headed out to somewhere,but where was the question?

Back at the Ostroff center

Serena's brother Eric sees Serena sleeping on a chair next to his bed and wakes her up. As he was excited to see his sister. "Serena... Serena." The younger blond male shouted softly trying to wake his sister as she was sleeping. Serena finally move and opened her eyes as she saw it was her brother and she had hugged him as he hugged back. "Hey how are you? The "It girl" asked her as she looked a little sad. Eric look back at his older sister and gave a small smile to her. " you know i"ve been better so where Naruto? The young blond had asked his sister as he gave her a look. To which Serena returned back as she said this "Eric, i know, i"ve been a terrible sister. I'm just happy to see you. And Naruto i called him earlier to come he said he was on his way." The blond "It girl" said as she gave a small smile and blush to the mention of her ex. Even though they were on and off at times Serena did regret some of her earlier choices she did when she was last here in the upper-side." It must of been a lot of rumors of why your back." Eric stated knowingly to his sister as he continued the conversation. "Yeah but none of them mention you."Serena said with a bit of optimism in her voice. Eric could only scoff when he heard that. " Just like mom wants hmm." Eric said very annoyed as he crossed his arms. Speak of the devil as soon as Eric said that Lily came in."What do i want. baby? For Serena sleeping in her own bed possibly wearing pajamas." The older blond said jokingly but was also annoyed.

Serena looked at her mother as she was confused by her mother's statement but greeted her anyways. "Moring mom, hey i was just about to ask the doctor if i could take Eric to breakfast. Wanna come?" The mother just scoffed at the idea."ehm no i think what i"ll do is get him a croissant down the street." The older blond said to her child as she walked out of the room. Serena stormed after her. "Serena don't." Trying not to make a big deal out of it. The problem was that Serena was not going to let it go."Let me guess, you told everyone Eric is just visiting grandpa in Rhode Island." She asked angrily. The older blond could only shake her head. "Your aunt Carol in Miami."Serena got more angry when she heard that news."So your'e actually hiding tried to take his own life and you''re worried it will cost you 'Mom of the year? The younger blond speculated as she was really pissed off with her mother.

"Serena you've been who knows what with god knows who..." The older blonder stated to her daughter. Serena looked at her mom and even more enraged."Look i told you boarding school was not like that." She said as she tried to convince her mom. Lily looked back at her daughter. "As happy as i am to have you home, you have no idea what it's been like.

Naruto then entered and heard everything. "now now ladies there no need for you both to cause a scene. I am sure there something we all work out and Lily is it really that bad for Eric just to be taken to breakfast that's all. Let the kid have some mobility at least is that to much to ask." The red head said as he gave both blond a devilish smirk and smile to which made them both blush. Lily looked back between Naruto and her kids and just gave a defeated sigh " just breakfast that it." Both Children were happy as Serena gave a radiant smile towards Naruto and hugged him. As they left the hospital to get something to eat. As soon as both Serena and Eric were going downstairs. Lily could only give Naruto a sly smile."So whats my favorite red head doing i thought you would mess around in the cul de sac." The older blond said with a little bit of lust in her voice. Naruto could only smirk at her." Lily control yourself you don''t want your kids to see you mess around with a young stud like me." The older blond could only roll her eyes as both of left the hospital to get something to eat.

* * *

 **Yes im back in action with my story bullshit and i wish you all a happy new year. Lets grow and shine and break our limits join me.**

 **So my fellow readers what did you think about this story, i will make this story a one paring by season if i go all the way with this story. So far this story is just a test and if its gets more love on it then i will continue it in 2019. Hope all of you have an awesome new year and rip Stan lee excelsior! Give me some more ideas as will try my best with each story. so tough melons to da kid and also listen to Imdontai- distractions he's the next x and ski mask combined. Then alos peep this guy Kemadagod- lane .**


	2. Chapter 2 - Piolt part 2

**I** **do not own the rights to either Naruto or Gossip Girl**

 **Chapter 2**

* * *

After getting something to eat both Naruto and Serena was walking together. The female blond had her had wrapped around the redhead as they were going shopping not that Naruto didn't mind at the slightest because he got a peek of what she was wearing every time. "So Serena when are you and Blair gonna makeup you know it hurts me to see to elites like you to be fighting." The red-haired boy said as he wanted to turn around as Serena was changing again in front of him not that she didn't mind Naruto staring at her but she still appreciated that he looked away and was not perving on her which was one of the reasons why she loved him. The blond pouted as she saw her friend turn away "Naru, you know Blair and you know how she is and especially what I did. I don't think she would forgive me." The female It-girl said as a tear was coming down her face.

This leads to the redhead male to hug his best friend. " You know I hate when you get upset but here something that should cheer you up why not go out with that Humprhey kid. The redhead said jokingly as some clothes were thrown at his face when he said that and he saw a blush of his friends face. Serena just decided to get back into her school attire as gave her second-best friend a kiss on the cheek and left. As she did Naruto saw a text from somebody and decided to exit out of the store as well.

At **The Palace Hotel** , Nate was waiting for Serena to arrive. It is revealed that Serena's family are currently staying at the hotel whilst their apartment is being renovated.

"Nate? Oh, hey. The female blond said as she went for a hug in a non-awkward way. As she wondered what he was doing here this early.

The young Archibald looked at Serena with a nonchalant looked "Uh, your mom told me you guys were staying here at the palace." He claimed as he wanted to get more but saw that Serena was looking a little unhappy.

"Yeah, uh, we're renovating again. You know my mom-If it's not broke, break it. So what are you doing here? The blond had asked him as she wanted to leave and get out of the situation of talking to him this soon. Especially when she hasn't patched things up with Blair yet.

"Oh, I just wanted to see how you were. You seemed kind of upset last night. The young brunette Archibald said as he was trying to get closer to her.

Serena took notice of this as she tried to back away slowly and said "I- I gotta get going and change for school. I'm gonna be late."

"Serena- No. No. But you're back now" Before Nate could continue his next sentence Serena stopped him there. "I didn't come back to you. "Look, Blair's my best friend, and you're her boyfriend, And she loves you. That's the way things are supposed to be." Serena said as she saw her favorite male friend walking towards her direction as she left Nate to his own devices.

As Naruto was walking up he saw Serena looking upset and normally he wouldn't pry too much into it even tho he knows what happened but he wanted Serena to tell him herself. Naruto gave his blond-haired a coffee as they were walking together to school. Serena showed a smile of appreciation for the coffee ." Thanks, Naru." She exclaimed as they continued to walk the redhead only nodded his head back in response.

 **Meanwhile on the Bus**

Nate and Chuck were talking, " Serena looked effing hot last night. There's something wrong with that level of perfection. It needs to be violated. You're telling me if you had the chance." Before Chuck could continue on how hot Serena was looking Nate stooped him there with a serious look on his face to his friend." I have a girlfriend." The young male said but Chuck only waved him off as he continued but wanted to talk about a different topic. "You guys have been dating since kindergarten And you haven't sealed the deal. Who says, "seal the deal"? Chuck said with a sly look on his face.

As they arrive at school, Chuck notices Dan behind him, "Are you following us or something? He asked as the black haired teen could only roll his eyes. Dan replies sarcastically, stating that they go to the same school, and are wearing the same uniform, which should be "kind of a tip-off."

 **Back at School**

Jenny Humphrey was

Before Blair could continue talking her face turned into a frown as she saw it was her ex-best friend with Naruto. Now she and Naruto were on good terms and apparently her mom liked the red hair as he had an eye for fashion. Also, he was the youngest author to have published a book with a little help with her mom. She didn't really mind it but to keep with appearance stake she doesn't talk to him like they use to before and if she were, to be honest, she with herself she would have dated the red-head.

"Hey. Here you guys are. I looked all over the dining hall for you. Oh, hi, I'm Serena." The it-girl said as she went to shake the younger Humphrey hand.

"I know. I mean, hi, I'm Jenny and hi Naruto. The younger Humphrey said as looked at Serena and then looked at Naruto lovingly with a blush on her face. To which made Serena only smirk at her best friend but no before getting back to the topic. B!" Serena said, with a huge smile lighting up her golden features, "Penelope was just telling me about your party. Kiss on the Lips? When is it?"

Blair smiled haughtily, not showing any teeth. Time to put this little bitch in her place. "The party's on Saturday. And you're kinda not invited," I simpered.

Serena's glowy smile fell. Blair was glad. She was a lot less beautiful when she wasn't smiling. "Why?" Seena asked with a frown on her face. "This is the first big party of junior year, I want to help you kick it off."

Blair brushed off her seemingly helpful comment. Blair was thinking that probably Serena just wanted to talk to Nate. "Because up until twelve hours ago, we all thought you were in Connecticut. Way to pull a fast one. Blair said as she still felt hurt from Serena.

And Jenny took our last invitation." Blair gestured to Jenny Humphrey, her newest intern. She had agreed to write all the invitations in calligraphy in exchange for one for herself. Blair could have easily added one more for Serena, but that would defeat the purpose.

Blair smiled cruelly at Serena once more. "That's it. We should be going," Blair called to her entourage, motioning toward school. Jenny hesitated. "Um, actually, Serena-" she started. Blair stamped on her foot to cut her off. "That's enough, Little J. Pipe down or else you won't be going to the party." Jenny then stopped talking as she snapped her fingers wanting a moment alone with her ex-best friend. Naruto seeing this decided to walk away so they could talk or do whatever they need to hash out. Blair and Serena were looking at each other as they finished talking Blair threw a smoothie on Serena's hair and walked away. Naruto saw this and slowly walked back up to his best friend.

Both Serena and Naruto just watched as Blair left. Naruto could only whistle in the display. "Wow, that was brutal." As soon as the red-head said that Serena only lightly punched his arm. It didn't hurt him but he could see the determination in Serena eyes of wanting her friend back. Serena gave Naruto the puppy dog eyes to which was cute but he would never admit towards his attractive friend."Umm Naru can i ask you a favor." As the It-girl only batted her eyelashes some more to drag it out to just made Naruto only raise an eyebrow.

* * *

 **Meanwhile at the other side of town**

For a first day on the job, Dan found this weekend, in particular, a major crash course in the life of luxury for the Upper Eastsiders. To his surprise, he had to help manage and throw together a scheduled cocktail party that was all for the promotion of Eleanor. Running around the corridors of the penthouse, Dan was eager and determined to make this the event of Eleanor's dream. When Eleanor had come in from her meeting, she hadn't said much during the set up so he was just thankful that he had least made it past the setup, but he knew just by the look of her that she would expect much greater things than just a great set up. Since he really wasn't all too prepared for the event, Darota had shown him to Harold Waldorf's, Blair's father's closet, to grab a casual suit so that he would at least look a bit like the rest of the staff. Heading into the kitchen to look over the food choices that were selected by Eleanor herself, Dan went down the checklist to make sure that each guest's requests were met. A moment of time was all he needed because he just couldn't wait to fill his dad in on the life of the rich and famous, oh the jokes that could be had between them when they got together

"You're doing good Mr. Humphrey" Darota praised him as she walked over towards him

"Really? You're not just saying that to me?" Dan asked "Because I can take you to suck and you shouldn't even be doing this" he then said making Darota laugh

"No, you're doing good. The suit even looks good on you Mr. Humphrey" Darota complimented him

"So is this a regular thing around here?" Dan asked as he looked over his list once again as the servers began taking the food out

"Very much so Mr. Humphrey…" Darota said before Dan interrupted

"You can call me Dan or Daniel," Dan told her "The Mr. Humphrey thing makes me feel like my father" he then said

"Well, Daniel. This is regular…this is routine" Darota replied

"And the whole Blair thing? I'm guessing she's the lion in the den" Dan asked

"Ms. Blair is not like that…most of the time. She has many layers, layers that no one has managed to pull back quite yet" Darota told Dan

"I wonder why" Dan replied as the final server went out

"The guests are starting to arrive, so If you have any last-minute things to do, then you better take care of them now. Ms. Waldorf doesn't like for staff to be wondering about" Darota warned him as he slowly backed out

"And I will take that as my queue to do my last-minute thing," Dan said before he made his way up the staircase. Looking around in search of the restroom, Dan did his best to find the restroom while he scrolled through his contact list to make a quick call to his father. Opening and closing the doors, he was becoming hopeful that the next door her came upon would be that of the restroom. In one swift motion, he opened the door only to find Blair and Nate in a compromising position in her bed. Quickly closing the door behind him, Dan could hear them scurrying about in the room before Nate finally came out of the room looking disheveled.

"Humphrey!" Blair yelled as she stormed out of her room "What the hell are you doing just coming into my bedroom! Have you lost your mind!" she yelled at him as Nate buttoned up his shirt as Dan did his best to forget what he had just seen

"I'm sorry. I was looking for the restroom. It was…I'm sorry" Dan babbled until they each heard Serena's name being said from downstairs. Freezing in the moment, Blair looked over at Nate, who seemed to be thrilled, giving Blair a quick glance, Nate soon took off downstairs with Blair close behind. Slowly descending the staircase to see the girl that he had spent a lifetime admiring from a far.

Wasting no time in pulling Serena in a cautious embrace, Blair stood back for a moment looking on at her best friend and her boyfriend hold each other as if they were long lost lovers or something. Standing at the bottom of the steps, Dan looked on from both Blair and the two so-called friends. Breaking away from Nate's embrace, Serena could feel all eyes on her as she slowly approached Blair.

"It's so good to see you," Blair said mustering up a smile for her friend

"It's good to see you," Serena said as leaned in to give her friend a hug

"Come, we're about to have dinner," Blair said as she broke away from her embrace

"I'll set a place for you at the table next to Blair, I'm sure you two have so much to catch up on" Eleanor said as she walked over towards the girls before Serena slowly backed away

"Yeah…that sounds good" Serena obliged as Blair grabbed her hand once again before Dan made his way over towards the doorway of the kitchen

"Daniel…" Eleanor looked to him to tell him but he quickly chimed in

"I'm on it" Dan replied before he stepped into the doorway of the "Can we have another place setting next to Blair please?" he asked as the servers immediately came out with the plate and utensils in hand as they went to set the table in the dining area. For a moment, Serena gave a lingering look at Dan as if she were trying to recognize him from somewhere at that point.

Dinner had run smoothly for everyone as the whispers slowly came to a halt once Blair had made it clear that for now, things were good with Serena. As of now Blair still remained the Queen Bee, so when it came to her laying down the law it was pretty much final amongst all and her minions. On occasion, Katy and Isabel would text a few tidbits of information to their social following but not much of anything negative was being said. As the guests began to filter out, Blair grew tired of wondering what was going on in Nate's head so when he offered to stay behind, she urged him to go out with Chuck for the evening. It was all becoming too much, too much for her to take in one day as she feared what Serena's presence would do to her but the whole social hierarchy that she had put into place. If one thing was for sure, she had to handle the matter that was Dan Humphrey…there was no way that she could deal with him, let alone deal with Serena. A good dismissal was what she needed and if it meant coming at the expense of a poor Brooklyn boy than so be it. Immediately walking into the living area where her mother was still entertaining guests, Dan slowly made his way out of the kitchen as he finished up for the day.

"I want him fired!" Blair demanded as Eleanor turned her attention towards her daughter

"Will you excuse us for a minute?" Eleanor asked as she rose from her seat to usher her guests off into another room that Dakota took them to

"He's got to go," Blair said sternly to her mother once the final guest had entered into the entertainment room while Dan stood back listening in on the conversation

"Why? Why does this one have to go now, Blair?" Eleanor asked becoming annoyed with her daughter's rant

"He walked in on me in my room. He didn't even knock, he just walked in like he owned the damn place" Blair replied

"Maybe he was trying to find his way around, the boy just started today" Eleanor replied

"And that decision I find makes your decision making a bit sketchy mother" Blair replied "I get that you want to help the poor, but give to a charity, don't hire one" she stated as Dan found himself clenching his fist tight together

"You haven't exactly made it so easy to just hire anyone. I mean honestly, you act like a common child" Eleanor said

"Because I'm tired of hire help running amuck in a place that is my home. A home that I'd like to feel comfortable in" Blair replied

"A home that contains a roof, that I work hard to keep over your head," Eleanor said

"And I'm eternally grateful to you for that, but this is getting ridiculous….he has to go," Blair told her mother once again before Dan had finally reached his breaking point and just had to step out from within the shadows and out into the open

"I'll go," Dan said as he walked over to grab his coat causing the two women to turn in shock that he had heard them

"Daniel," Eleanor said as began to put on his coat

"See, he just lurks around like he owns the place" Blair stated before Eleanor brushed past her daughter and over towards Dan

"Look, I don't know what happened…" Eleanor said before Dan quickly interrupted

"I was looking for the restroom. I couldn't find it, so I kept opening doors….I should have knocked but I just thought everyone was downstairs. I opened the door and saw Nate and Blair on the bed together" Dan said as Blair's eyes nearly bulged out her eyes with his reveal of her actions in her room

"Doing what in your room?" Eleanor turned to ask Blair

"Privacy, you know I should be able to have that in my house, my room…but with Humphrey that's been under attack since the moment you hired him," Blair said making Dan even more annoyed

"If I could just get my pay for the day, I won't cause a scene…I'll quit," Dan told Eleanor who seemed to be in a bind

"Would you like that in quarters?" Blair asked as she reached for her purse "You know for bus purposes" she said

"No" Eleanor simply replied leaving both Dan and Blair confused

"No, to what?" Blair asked "I can give him my singles, but I hear on public transportation they prefer the coins," she said

"No, as in your not quitting," Eleanor told him as Blair stood in disbelief

"Does my opinion not matter around here?" Blair stated

"You will get used to him because I'm not firing him nor is he quitting," Eleanor said "Daniel, I hired you because you are by far well suited for this position and for your age I think you are wise beyond your years," she said

"Which only amounts to sixteen, how much wisdom do you get at that age?" Blair said sarcastically

"Dakota will get you aware of the house as far as where things are and how things go tomorrow, so that will take you out of Blair's way" Eleanor said as she looked from both Blair and Dan "I expect my daughter to be on board with this decision, and I pray that she will not cause any problem because if she does…I guarantee that there will be consequences" she said

"Consequences? That's a joke if I ever heard one" Blair sneered at her mother as she walked over to the staircase "You wanna lay down the law…then be a mother and stay at home, then maybe you wouldn't have to hire so many people to tend to your responsibilities" she said before she stormed off upstairs to her room. Hearing the elevator doors open up, both Eleanor and Dan turned back a bit surprised to see Serena make her way inside. Walking cautiously over to the two, she began to wonder if she was interrupting a moment.

"Should I come back later?" Serena asked cautiously

"No, no. I think you might be the only one to calm her down" Eleanor sighed

"What happened?" Serena asked as Eleanor looked on at Dan then back at Serena

"I'm sure she'll inform you" Eleanor sighed "I have to get back to my guests, but I will be expecting you tomorrow Daniel…am I right in that assumption?" she asked

"No, I won't be here tomorrow because it's my day off. I'll be here Monday after school" Dan replied as Eleanor smiled at him before she headed into the entertainment room to join her guests leaving Daniel and Serena behind.

"So your name is Daniel?" Serena asked him

"Yes, the name is Dan Humphrey" Dan introduced himself

"My name is Serena…" Serena began to introduce herself before he cut her off

"I know, I know who you are" Dan replied

"Right, because of Gossip Girl" Serena concluded, "I told her to use my best pictures, so that's our trade-off on me constantly frequenting her blog," she said as Dan and he just laughed.

"I should be going, it's late and I'm pretty sure Blair hates me by now," Dan said

"I wouldn't worry too much about Blair. She's a bit much, but she's worth it" Serena smiled weakly

"Well I have quite seen that side to her, and I'm not sure its there for a Brooklyn boy like me to see in the first place," Dan told her "It was nice to meet you, Serena," he said before he made his way over to the elevator

"Could you do me a favor?" Serena asked as she turned towards him

"Yeah, anything" Dan replied quickly realizing that he sounded pathetic "I mean, what?" he corrected himself

"Pick me up at eight" Serena told him "The Kiss on the Lips party is tomorrow night, and with me coming home at a late time made it nearly impossible for me to find a date. So will you please do me the honor of being my date?" she asked with a look as if she were begging him, which was surprising to him since he should have been the one begging her

"Sure, I'll go with you" Dan replied as a slight laugh came to his face "You really go out with some guy you don't know?" he then asked her as she just flashed the million-dollar smile that made her the Serena van der Woodsen he had loved fo so long

"Well, you can't be worse than the guys I do know" Serena smiled as she ascended the staircase with a bit of flirty smile on her face as she looked on at Dan.

Things were trying to get back to normal or at least Blair was trying to let it be, but she couldn't help but have a firm hold on her present, which made her the Queen Bee. If she had to go over what scared her the most, she feared that losing Nate may have been high on that list of what Serena intended to get back. At the time she thought she was crazy, but it was the way he looked at Serena that made her question herself over and over again. Ever since they were little, Blair had always been behind Serena when it came to everything anything in their lives. She had accepted that she would always be second best to Serena van der Woodsen, but when she had left…a part of her didn't feel as overwhelmed with sadness as she had thought, but she felt like it was her time to step into the role she always knew she could be. Now, sitting at breakfast with Nate, she began to wonder once again if her relationship was as strong as she thought.

"Are you going to finish your food?" Nate asked

"I'm not that hungry" Blair replied "I talked to Serena last night" she then mentioned

"Oh, what did she say?" Nate asked becoming intrigued with the conversation

"Nothing much, we mostly caught up," Blair said as they continued to eat on in silence before she looked over at him to see that she had once again lost his interest "She asked about you though" she said deciding to take the route of lying to see where that got her with her boyfriend

"What about?" Nate asked as he put his fork down to look at her before wiping his mouth with the napkin

"Just how you were. She was concerned, is there any reason to be concerned?" Blair asked

"We're all friends. I mean its only natural that we'd be concerned about each other" Nate replied

"Yeah, but it just seems like she knew something I didn't," Blair said "Is there something you should tell me?" she asked

"Nothing that comes to mind," Nate said "Look, Blair…" he said grabbing ahold of her hand before her cell phone went off and she reached for the phone

"It's Isabel. Some girl asked her for an invite to the Kiss on the Lips" Blair scoffed at the notion that some random thought they were welcome

"I thought you had extra's made by that freshmen?" Nate asked

"You mean that Jenny girl…yeah, but I only gave those extras to a few of the Dalton girls…their fathers happen to be board members on the Yale Alumni" Blair smiled proudly

"Did you give one to Serena?" Nate asked

"No" Blair replied "S, barely came back when the invites were issued…I can't just up and have one made" she said

"Why not? She's your best friend…and its Serena for crying out loud" Nate said

"So? Nate, she had an ample amount of time to confirm her appearances. I can't just make exceptions" Blair replied

"What's this really about? Because we both know you can if you wanted to, and it just sounds like you don't want to when it comes to Serena. It's like your trying to ignore her or something" Nate said

"Maybe I'm not ready to be her lackey again, Serena left and now she expects people to fall in line because she's returned…it doesn't work that way, and you shouldn't expect me to" Blair said

"Serena doesn't deserve this" Nate replied

"And neither do I. You're supposed to be my boyfriend and yet you sound like hers. Am I missing something here?" Blair asked as she glared at Nate

"Like what?" Nate sighed as he asked her

"The truth. I want the truth, because I have this feeling like I don't have it" Blair said "So I'm asking you, Nate Archibald, what is your deal with Serena?" she asked

"I'm just tired of you being hot and cold with her, that's my deal," Nate said as he got up from his seat to throw his napkin down "I'm gonna go get the check" he muttered before he walked off leaving her by herself.

 **Meanwhile somewhere else**

Looking over his ties in the mirror, Dan still was in disbelief that he was actually taking Serena van der Woodsen out to the Kiss on the Lips party. He was just surprised in general that he was being near Serena let alone taking her out. His perception of Blair and Serena seemed like night and day. With Blair, it was everything he hated in the Upper Eastside, and with Serena…it was like she was giving the Upper Eastside a new face, a face that seemed so welcoming and that it didn't matter your parent's income in whether you were worthy or not. As a writer, Dan had written stories upon stories about the beautiful blonde and how she had captured his heart the moment he laid eyes on her at a tenth birthday party. It had been an accident that he was even there in the first place, but of all the people there she was the only one that had even said a word to him, and at that moment he fell hard for her. Coming out of his room with his tie selection in hand, Dan joined his father and sister in the kitchen for their daily banter.

"Guess who's a dad is cool?" Rufus asked his son as he took his seat on the stool

"It's a trick question" Jenny laughed at her father

"Yeah, because it can't be ours" Dan replied as he began to play with his tie once again

"Look at this!" Rufus declared as he handed over an issue of Rolling Stones

"Top ten forgotten bands of the nineties" Dan read aloud

"And check out who's number nine," Rufus said proudly

"He is very proud" Jenny smiled

"Way to be forgotten dad" Dan laughed at his father as he closed the magazine

"Thank you, thank you very much," Rufus said as he began to bow as if he had an imaginary audience "Being forgotten on is list is how you get remembered" he then said

"Or it could just mean your forgotten" Dan teased

"Maybe he'd care if it was on Gossip Girl" Jenny teased her brother

"What? I don't read Gossip Girl….that's for chicks, and I don't…" Dan said before Jenny chimed in

"Sit up until the wee hours of the morning reading about Serena van der Woodsen," Jenny said

"Way to go, dad, I mean this is a big accomplishment," Dan said turning his attention towards his father

"Where are the little cards that you were working on?" Rufus asked

"You mean the Kiss on the Lips party," Jenny said "I gave them to Blair all ready. Everyone who is anyone is going to that party" she said

"Uh, if I never hear the name Blair Waldorf again" Dan groaned

"Blair Waldorf" Jenny quickly replied "Do you not know who she is?" she asked

"She's something I don't care to call a woman, but with her, it's completely justified. She's like a mini dictator, who tried to get me fired. Luckily her mother likes me" Dan said

"Mini dictator" Rufus laughed to himself "Makes me think of Napoleon Bonaparte" he smiled as both Dan and Jenny looked at him confused by the reference "What? That was the only thing I picked up in high school….anyways, continue about this Blair girl" he said trying to cover on his awkward

"Blair Waldorf is essential to your imaginative future with Serena," Jenny said

"How is that?" Dan asked becoming amused with her dramatization of Blair

"Because Serena and Blair are best friends," Jenny said

"Didn't seem that way at work today. Blair seemed like her worst nightmare had come to life" Dan said

"That's right…you hob knob with the rich and famous now" Rufus laughed

"As well as deal with the many scowls of Blair Waldorf. Hell has created a job and sent its favorite demon to lurk over it" Dan joked as both Rufus and he laughed while Jenny looked like he was insulting her idol "It's a joke, Jen. Laugh. Chuckle. Do something" he said hoping his sister would lighten up

"She's really nice once you get to know her" Jenny defended

"I'm sure, after the many, many, many layers you have to peel back she is," Dan said "Besides, Blair is not my concern because I am going to have the night of my life tonight" he then said

"And why is that?" Rufus asked

"Because I'm amongst the anyone, who will be going to the Kiss on the Lips party" Dan declared as Jenny nearly fell over in shock

"How?" Jenny asked

"Serena van der Woodsen's date is how" Dan smiled "See, I'm already going around the whole Blair issue" he smiled as he took a bite out of his pancakes that Rufus had put out for them

 **On the Upperside**

It had been days worth of planning for the brunette because tonight was going to be one that she would never forget if it went according to plan. She began to think that it was all in her head, that maybe she had truly had her best friend back and that her being back would be the icing on the cake to her being the Queen. Tonight of all nights had to perfect just for her sake.

On the ride over to the Kiss on the Lips, they were living it up like they were rockstars. They were the Upper Eastsiders, they did things that only people dreamed they could do at that age. Finally pulling up in front of the party, they had made their way in like they were royalty with all eyes on them. Grabbing a few drinks from the bar, they all gathered around looking on at the extravagance that was Kiss on the Lips party. Enjoying the laughter and the all-around good time with her friends, Blair has quickly torn away from her happiness when she saw Serena come in with Dan Humphrey. Turning towards Nate, who motioned to walk over towards them but she quickly put her hand up to stop him. Blair found herself in a state of confusion because she swore she saw the same look she had been seeing every time he saw her face.

"She brought the help, unbelievable," Blair said to herself before she turned to look over at her boyfriend who once again seemed to be in awe of Serena van der Woodsen like she was the Queen or something "Did you do this?" she then asked

"What?" Nate asked in confusion "Blair c'mon, don't start this" he replied not wanting to get into another argument about what she suspects is going on

"Did you do this?" Blair asked ignoring his plea for peace "Did you invite Serena?" she asked

"I'm sure she knew about the party, we have it the same time each year…nothing has changed" Nate defended himself

"Something has changed because it's on your face every time she comes into a room" Blair replied

"You're being paranoid" Nate replied

"Don't patronize me" Blair replied

"I'm not" Nate refuted

"Stay away from her" Blair said

"You have nothing to worry about" Nate replied

"Really? Because I never thought I had anything to worry about, but when you get that look on your face…it makes me think, are you being honest with me? About everything? About Serena?" Blair asked as Nate took a moment to think before answering

"Yes. I'm being honest" Nate replied unconvincingly

"Why don't I believe you?" Blair asked as tears welled up in her eyes as Nate couldn't think of a thing to do that would make her satisfied at this moment. Turning towards Chuck, who was flirting with a batch of newbies, she made her way over towards him. "I want some," she told him

"Some? You're going to have to be specific" Chuck replied

"You know what I'm talking about. Meet me in the backroom in ten minutes" Blair told him as she brushed past Nate and made her way to the back room.

Even Naruto was at the party but he to busy but his eye did catch that both Serena and Nate were together. Naruto saw Dan and the black-haired teen approach him which was pretty big of him to do. Dan went to shake Naruto hand to which also surprised the redhead but complied and did the same back. " Look Naruto I really like Serena and i know both of you guys are really close so i just wanted to say that out up in the open." Naruto could only laugh at Dan but decided to entertain him, " you have nothing to worry about Dan and besides where is Serena now at the moment." The redhead asked to which made Dan put a hand in a thinking motion as he didn't know so he left in search for the blonde.

Dan had told the father of his day climb of the social ladder, but never in a million years did he think that he would have gotten to escort Serena van der Woodsen to the Kiss on the Lips party. Though he had practiced over and over in his mind the funny things he would say to her that would make her swoon, he found the night to be a bit of a cat and mouse chase. One moment he would have Serena in his midst but then she'd drift off giving the excuse that she was going to freshen up. This had gone far from his dream date, but he knew that along with the pressure of returning back to Gossip Girl territory, Serena couldn't just slip back into her old life like it was nothing. He could hear the whispers in the crowd that would speak of the prevalent rumors and even the newly created rumors that had formed about her. A piece of him felt for her because no matter what she tried to do, there was always going to be some part of her past that was going to haunt her. Heading over to the lounge area to grab his wallet from his coat pocket. Finding the door a bit jammed, Dan gave the door another budge before he opened it up to see Nate and Serena together.

"Dan," Serena said as she broke away from Nate's embrace

"I should go," Dan said as he walked over to grab his coat after a moment of silence came between them all.

"Dan, you can't…you can't tell Blair" Nate said as Serena quickly hit him

"Don't worry. Your secret is safe with me" Dan replied sarcastically but found their actions to be repulsive

"Dan, this isn't what you think" Serena replied

"I really don't care what you have to tell me at this moment, but I think I understand why you ask guys you don't know out," Dan said "Because you use them as a cover to see your best friends boyfriend behind her back," he said as he put his coat on

"Dan, I'm sorry" Serena apologized

"Don't apologize. Just…just forget I was even here" Dan said before he left the room.

Making his way through the crowd of people, Dan had finally managed to get outside. He could curse himself for actually thinking that he could fit in this world, he was a boy from Brooklyn and that's where he wanted to remain and tonight only reinforced that. Standing out waiting for a taxi to pull over, he could hear rumblings from the group of girls next to him about Blair. A bit of laughter came to his face as the Queen Bee herself wasn't even that well-liked by her fellow classmates. If only they knew what she was like at home? He thought to himself, well she deserves it because you can't go around treating people like crap and expect to be liked. His jokes turned to a look of concern as the conversation the girls were carrying on turned to what she was doing in the back room. There was no reason to care, but he could hear Eleanor in his head reprimanding him for not seeing that Blair wasn't keeping herself out of trouble. Why should he have to care about Blair? He asked himself a million times, but then he realized that maybe rescuing Blair from herself would look good in Eleanor's eyes and only solidify to her that he was a good hire. Taking a deep sigh of frustration, he made his way back into the party to where she was rumored to be. Shaking his head in disbelief, he could only imagine what she was doing that was all sorts of illegal. Opening up the door to the backroom, he rolled his eyes in annoyment as he just thought that this was all they did…cheat on each other, do something stupid, and cheat on each other.

"Get off of her" Dan said as he grabbed Chuck and pulled him off of a passed out Blair

"What the hell is your problem!" Chuck yelled

"At this moment, it's you" Dan replied "Back away," he said as they were becoming close to throwing down

"Or what?" Chuck asked before Dan let out a laugh then pulled back to punch Chuck

"I don't like you," Dan said as he stood over Chuck's body before making his way over towards Blair to help her up while she still remains knocked out. Supporting her body up against his, he took the back way out so that no one would see the quote on quote Queen Bee in this state. Stepping out to the sidewalk carrying an unconscious Blair Waldorf seemed to have done the trick in hailing a taxi because it took no longer than two minutes before a taxi pulled over towards them. Putting her into the car first, he could only imagine what the driver was thinking as he saw how passed out she was but luckily the driver had seen enough drunken rich kids that it was almost abnormal to not see them passed out. As they drove back to her building, Dan looked out the lights of New York wondering just what exactly the cruel joke of the weekend was supposed to be for him. Trapped in a cab with a passed out Blair Waldorf. Getting played by the girl of his dreams. Working for Blair Waldorf. Oh, and the thing that made him curse at himself even more…thinking this world would fit with the world he knew.

* * *

Naruto had just got back from the party and boy was it crazy. As he was about to lay down he felt another body cuddling up to him to which only made him smirk."How many times have i told you not to pick my lock, Georgina." The blond said with a frown on his face but the now black-haired madden could only smirk back and give Naruto some kisses. "You know i can't do that and how is my favorite blond doing and when can i get my revenge on her?" She had asked but Naruto could only give her a deviant smirk as he gave her another powerful kiss and both were kissing and battling for romance. "You Know Georgina there really isn't any need for you too do that but a deviant prank will suffice." The redhead proclaimed as he and both Georgina laughed and layed in the bed with both the warmth of their body. "Enough talk I want my main course" Georgina stated as she lowered her head in the sheets. Yeah, it was gonna be a long night.

 **Gossip Girl Voice "** **Spotted - Serena making a heroic exit From b** **'S party.** **Too bad for her there's school on Monday. What does our favorite fox have cooking up?** **So until next time- You know you love me - xoxo Gossip Girl.**

* * *

 **Author notes**

So I been trying to get this story going and it's been hard I'm not gonna lie and this is not a harem but Naruto will go out with several people throughout the season if i continue this story. Just give me somebody you want me to pair Naruto with and I'll probably do it. since not too many people are doing this story and also I will improve on this story some more.


	3. Chapter 3

**I bet you're wondering what Gossip Girl is doing up so early. Truth is, I never went to bed. Why waste precious time dreaming when waking life is so much better. Is there really anything better than a lazy Sunday? Reading the paper in bed, sipping coffee, scrambling an egg or two. Yeah, right. We Upper East Siders don't do lazy. Breakfast is brunch and it comes with champagne, a dress code, and a hundred of our closest friends. And enemies. Chuck's dad, Bart Bass, is hosting the annual brunch for his foundation. Everyone is invited. Well... not everyone.**

 **-Gossip Girl**

Slowly sitting up in his bed still half asleep, Dan reaches over towards his ringing alarm clock and turns the alarm off as he reluctantly realizing that he was awake. Take a deep sigh knowing that he couldn't enjoy the lazy day he had planned for himself just before school started up, he steadily made his way out of bed and headed over towards his window to look out on the city. With the sun shining brightly on him, he turned and made his way to the restroom to start getting ready for work. He hadn't planned to ever work on Sunday, just because there was only so much of Blair Waldorf that he could handle, but last-minute items had been faxed into Eleanor that was pressing for him to get out before the deadline or else. Reaching for the lights in the restroom, Dan grabbed his toothbrush before he finally got a good look at himself in the mirror realizing that he looked like he came straight out of hell just by how tired he looked, and after his night with Blair Waldorf…it truly felt like he came from the devil's cage he thought to himself. Feeling a twinge of pain come from his arm, he lifted the sleeve of his shirt up to see a bruise beginning to form on his arm but he couldn't help but go back to looking at his face. Just as he began to play with his facial features wondering if he was getting wrinkles, Jenny couldn't help but laugh at her brother as she entered the restroom.

"You're up early" Jenny smiled as she reached for her brush to begin combing her hair

"I'm up in general" Dan shrugged before he looked to see that his sister was dressed as if she were hitting the town "What's with all the clothes?" he asked as he put toothpaste onto his toothbrush just before he ran water over the brush to start brushing his teeth

"This is usually what you wear during the day" Jenny laughed as she answered sarcastically

"Where are you going?" Dan reiterated to his sister

"I'm going to see a friend" Jenny replied

"This early? Who is this friend?" Dan asked.

"A friend," Jenny said.

"You do know how this will go right? Your answer in brief but short sentences, then I'll just ask another question that will try to get to the heart of what I want to know….so I think it'd be best if you just tell me and we can end all the speculation" Dan told his sister.

"I'm going to see Eric" Jenny sighed as he turned to look at her with much shock on his face.

"Eric? That guy you've been e-mailing?" Dan asked.

"Yes," Jenny said as she began to pin her hair up.

"Is this like your boyfriend?….how come I haven't met him yet?" Dan asked.

"No, he's not my boyfriend….and he's not really in the position to meet people voluntarily" Jenny replied.

"Okay, that makes me a bit worried. Why can't he meet people voluntarily? He's not some criminal is he?" Dan asked.

"What's with the twenty questions Daniel" Jenny told her brother.

"Jen, you're going to see a guy that I know nothing about or know little about…I just want to know" Dan said.

"Will you just trust me. There is nothing you need to worry about or secretly tell dad about. I promise you that, he is a friend, and I'm going to visit him for an hour tops" Jenny said

"I do like the time limit, that makes me feel better" Dan smiled

"But imagine the things that could be done in an hour" Jenny teased her brother

"Please, please, don't put that image in my head," Dan said clenching his eyes shut in horror at the thought of his sister even in that manner was just horrible

"How was the party? I heard it was epic due to Serena of course" Jenny asked as he just laughed to himself

"It was epic alright," Dan said thinking back on catching Serena with Nate

"Give me the details, don't hold out?" Jenny asked

"Basically a bunch of rich kids dressed up in what is the amount of rent we pay time five, drugs, alcohol, lies, and me being stuck taking Blair Waldorf home" Dan replied as Jenny just sat in admiration

"You took Blair Waldorf home, I'm officially happy for you" Jenny squealed as she hugged her brother in excitement catching him off guard

"Jen, it wasn't like what you think. I hated it" Dan said

"You make Blair out to be like she's some evil bitch or something" Jenny replied

"If the shoe fits, but lets state for the record that those were your words, not mine," Dan said

"How bad could it have been?" Jenny asked as Dan just stared at himself in the mirror before feeling another twinge of pain in his arm, which was probably a delayed reaction of Jenny pressing her body up against his arm.

Nibbling on a piece of fruit as she looked out at the window, Blair couldn't help but drown out the noise of the cleaning staff with their vacuuming and the clitter clatter of dishes going on within the kitchen as this had become her usual routine in the morning. She had always been around staff, hell it was abnormal to some less than her to even have the word staff in the regular vocabulary, but for a girl like her, an Upper East sider, parents were a noun regularly replaced with the word staff. Darota, her loyal and trusty maid, had always held a special place in her heart just because of the fact that she was the only constant in her life. She had known the young Blair all the way to her transition into the complicated world of womanhood, so she had come to think of Darota as her family, the constant family that wouldn't leave. Doing her dusting around the living room, Darota looked back at Blair to notice that she had hardly touched anything on her plate as her mind was clearly elsewhere.

"Ms. Blair, you should eat something" Darota recommended to her as she leaned over to grab a raspberry to oblige her to wish

"There. I've eaten" Blair replied sarcastically

"Security mentioned that they saw you stumble in early this morning, is Ms. Blair still full of consumption?" Darota asked as Blair just scoffed at the thought that nothing remained a secret around her

"If you must know, I did have one too many but I didn't stumble in…I'm a lady, I would never do such a thing" Blair replied as classy as she could due to the circumstances

"Was Mr. Nate the boy that escorted you in?" Darota asked becoming interested in the events of last night

"I don't remember…I was under consumption, remember" Blair replied as he cell phone began to ring "I see my minions are up" she sighed as she answered her phone "Hello" she answered tiredly

"Can you believe that she actually showed up?" Katy asked still in her school girl crush mode of excitement

"Can you not scream in my ear, people do like to be talked to in a normal voice" Blair snapped at her minion "Now, please tell me she is not babbling about Serena?" she then asked Isabel knowing she was on the line as well

"It's all the buzz. Have you checked Gossip Girl?" Isabel asked before Blair looked over at Darota and mouthed for her to pull up Gossip Girl before Darota dropped her dusting duties and got right on task. Bringing the laptop over, Blair read the update about the wild Kiss on the Lips party

"So she's achieved her goal. Gain buzz, now why has she returned is the true question" Blair said to herself as she became less and less enthused to see her best friend all ready regaining her role as buzzworthy on Gossip Girl.

"You don't sound too happy" Katy replied.

"Because she committed a social crime last night. Never crash a party, that's for the classless and…" Blair said just as Dan stepped off the elevator and made his way inside to greet Darota "And the Dan Humphrey's of the world" she said becoming annoyed with his presence as he just strolled in like he belonged, making nice with Darota as if they were now BFF's.

"That is true, party crashing is the so late nineties" Isabel reiterated making Blair surprised at how they latched on to her words and made it seem like it came from the Bible by the amount of importance they put to it

"But didn't they make a movie about it, Wedding Crashers" Katy replied missing the point "It was really funny, its one of my faves" she said happily

"Katy, your voice" Blair said as she began to massage her head

"What about it?" Katy quickly replied

"It's annoying me. Lets put it on mute for two minutes" Blair told her as she put her lap top down on the coffee table "I don't want to see Serena at school, and she better not show up at brunch today" she stated

"Your really mad at Serena" Isabel stated "I hope you never get that mad at us" she then said

"Well, you'd never do what Serena did" Blair replied as Dan nervously looked on at her when she had made that statement unsure if she knew what happened last night or not.

"No, never" Isabel quickly replied "Katy, you're supposed to reply" she whispered to her friend

"I'm supposed to be on mute" Katy told Isabel as Blair just shook her head at the stupidity they seemed to put on full display at times

"Bored now, I have to go," Blair said becoming tired with their banter before she hung up the phone. "Humphrey, what are you doing here? I thought it was agreed upon that I would get my rest of you on the seventh day" she asked

"That is the arrangement, so don't worry I'm not here to disturb your delicate sensibilities," Dan told her.

"I try to do what I always do when it comes to you, pretend you don't exist. Then again I never had to pretend because you don't" Blair replied.

"Don't you think a thank you is in order?" Dan asked her.

"A thank you, I didn't see that in your contract, maybe you should take that up with Eleanor" Blair replied.

"No, I think its suppose to come from you," Dan said as he was looking at her.

"You'll reach death before you get that" Blair replied.

"So let's just forget the fact that I had to rescue you from a disturbing hook up with Chuck Bass, Nate's best friend. Then got brutally beaten the whole time I brought you up" Dan said as Darota looked on at Blair in shock.

"It was Mr. Humphrey?" Darota asked in shocked not believing it.

"Call the driver, and tell him I need to run to Marc Jacobs" Blair said quickly getting up from her seat "Then call Nate and remind him about brunch because he has a tendency to forget" she said completely ignoring the statement as Darota just looked at her "Now!" she demanded before Darota motioned to move but Dan stopped her

"I'll do it," Dan said becoming irritated with Blair's behavior just as he made his way into the kitchen

"Follow him, high and mighty might screw up the request," Blair told Darota as she headed into the kitchen. Making her way over to the elevator, she hit the button but couldn't seem to shake Dan's self-righteous behavior. Like she owed him anything she thought to herself. The last thing she owed Humphrey was revenge, and maybe that'd have to be bumped up on her list of things to do for the day before the brunch. Just as the elevator doors opened, she ditched boarding and made her way inside her mother's office. Making sure to leave a crack in the door so that she could hear if he was coming, Blair began to sift through her mother's files before she finally found Dan's file. Opening up the file she couldn't help but smile as she had access to his background information within her grasp "Let's see what you've got in your closet Humphrey" she said to her self as she leaned back in the chair beginning to read on.

Hearing a ding sound come from outside of the kitchen, Dan sighed in frustration as he could only imagine what another mundane task Blair would want to be done now. The average decent person would have said thank you for assisting me in my drunken stupor but he felt even more stupid to think that decency could go along with Blair in the same sentence. Heading out into the living room not wanting Darota to catch her wrath for his earlier comments, he opened himself up to be the slave for the day on top of completing the assigned task by Eleanor. Once he made his way out to see who it was, he couldn't help but laugh as his day had just got more absurd by the minute with the presence of Nate added to the mix of the day. He could instantly see that Nate was caught off guard, as he didn't know whether Dan had spilled all to Blair or was just here due to work.

"What are you doing here?" Nate asked confused

"That's two for two today," Dan said to himself "Don't worry, I didn't run to come to tell Blair about Serena and you," he told Nate. Hearing Nate and Serena linked in the same sentence quickly tore Blair away from her snooping in her mother's office as she was faced to deal with whether she should continue listening or make her appearance known to force a confession out of Nate. The ideas both seemed doable but she knew if she was ever going to get answers then she would have to remain in this position.

"Look, about last night…it was just a moment" Nate replied in his defense.

"Shouldn't you be having those moments with your girlfriend, not Serena" Dan quickly replied as Nate ran his hand through his hair in complete confusion

"I know, I know" Nate sighed "I tried to tell Blair, but I couldn't," he said.

"So that paved the way for you to make out with Serena last night. Trying doesn't mean you completed the task" Dan said. Hearing those words nearly made Blair fall to her knees as her suspicions had been confirmed, something was going on with Nate and Serena.

"Serena and I…it was a moment, like a caught up in the fact that we haven't seen each other type of deal. I love Blair, I want to make things work with her" Nate said

"I'd believe that if I wasn't used for the cover, which makes me believe that there is more to this story," Dan said "I'm not stupid, you people may think I am but I know when I've been used. Serena van der Woodsen all of sudden asks a guy she barely knows…c'mon, sounds like a set up" he said

"You sure you don't know a thing about this world" Nate laughed

"It isn't funny" Dan replied as he folded his arms

"And I'm not trying to make it all one big joke. I just need a favor from you?" Nate asked

"More favors? You really don't get it, do you?" Dan asked in disbelief

"Look, I understand that I'm an ass and everything under the sun that makes me horrible, but I will tell her the truth…I just need time, today to be exact" Nate said

"Today?" Dan asked

"Before brunch. In fact, I even came by early to talk to Blair" Nate said

"Well she's out shopping at some Marc place or something," Dan said as Nate just laughed

"Marc Jacobs, I know where that's at" Nate laughed "So how about it? Do I have your word?" he asked

"Sure. Fine, whatever. I won't tell" Dan replied

"Thank you," Nate said before he turned to head towards the elevator

"At least I got a thank you from you," Dan said to himself as Nate got onto the elevator "Darota, we should probably hide the liquor. I foresee a rough night for Blair" he called out as he headed into the kitchen.

Leaning up against the door in total disbelief, Blair tried to hold back the tears that were coming to her. Over and over in her head, she kept telling herself that she wouldn't cry, she wouldn't shed a tear over the damage that Serena has caused all in the span of her return. She was the fool, in this whole mess she had gone from the Queen to the fool, even Humphrey was making her out to be the poor little victim. No, if she was going to go through this so-called brunch, she wasn't going to be attacked…she was going to attack back. One by one.

* * *

 **Gossip Girl: Looks like the tables are all set. As soon as the guests arrive, we can start dishing. We hear revelations are the appetizers, betrayal for a side, and exposure is the main course. Yum, sounds good to me.**

Meanwhile with Jenny

It always surprised Jenny how down to earth Eric truly was, it was like the fact that he could buy anything at will didn't even phase him…hell his sister being home and stirring up some drama didn't phase him one bit. She originally had just thought of Eric as some regular boy, when they first started talking but it was until he revealed the tidbits about his family that she soon realized who he was. Any outsider would have lamented at the prospect of being close to a Van der Woodsen, but she knew that she couldn't use Eric like that. Recently Eric had done something that he wasn't exactly proud of that landed him the Ostroff center, he hadn't said much about it but Jenny knew that it had to be serious in order for him to be in the Ostroff Center. She'd come by regularly to do school work with him that they were assigned over the summertime, but she never questioned as to what brought him here. It was just something she did to make him feel like everything was normal at least with her each day. Coming out of the center, Jenny was a bit surprised to see Blair Waldorf outside.

"Blair?" Jenny questioned as Blair looked on with surprise to see Jenny there.

"Jessica" Blair replied as she didn't really care with what she heard from today.

"My name is Jenny" Jenny corrected her as Blair tried to play off like she did that on purpose "What are you doing around here?" she then asked.

"I was meeting a friend" Blair lied as she soon noticed an Ostroff visitors tag that read Van der Woodsen on it that was on Jenny before Jenny quickly pulled it off of her

"I forgot to take this off" Jenny laughed at herself.

"Oh, it's okay. We all forget to tear of rehab clinic name tags" Blair replied.

"It's not for me, I was just coming to see a friend," Jenny said.

"Aren't you on that homework delivery program?" Blair asked becoming more intrigued with Jenny by the minute

"You mean taking assignments to students, the student to student care program?" Jenny asked.

"I thought that's what I said" Blair started feeling as if she was only hearing a repeat version of her previous question "Tell me, who gets the homework assignments…I mean technically since school starts up tomorrow, it would have to be to a student who wasn't previously here, right?" she asked.

"Yeah, it basically goes to a student who has been absent for a certain amount of time, of course, their parents have to put them on the program so they can ensure that the student is enrolled and yada yada yada" Jenny replied as Blair smiled as if she had caught on to something big

"I think it's great that you do this. I mean not a lot of people I know to partake in school activities, but you, Jenny…I'm sorry, I don't know your last name" Blair said

"Humphrey" Jenny replied quickly as Blair just became overjoyed realizing that she had two for the price of one revenge.

"Jenny Humphrey, why didn't I put it together in the first place. Your Dan's sister, right?" Blair asked.

"Yeah, I don't really like to tag on to my brother too much because you know, I want to make friends on my own merit…if that makes any sense" Jenny babbled

"It's fine. I mean your brother…he's words that I can't seem to describe in the present moment or at least to you, but a girl has to step out of the sibling's shadow" Blair replied

"Yeah" Jenny smiled

"Look, if you're not doing anything, I was wondering if you could come with me to the Bass Brunch today….but I don't want to mess with any plans you already have," Blair asked.

"No, no. I'm not busy, I would love to go" Jenny said excitingly.

"Great, that'll give us a chance to talk" Blair smiled and that's all she needs to hook and bait the fish.

 **On the other** side **of town**

Naruto had just got off the bed. The young male was looking around as he had just seen a couple of notification on his phone. He also saw that Georgina was no longer there she probably went back especially with how her parents are. As Naruto was in thought he heard a knock on the door. He slowly went to open it seeing it was Serena and it seemed that she was upset. " What's wrong Serena?" The red-head had asked he had just gone into the shower and she followed him into the room. Serena looked at her best friend and told him about how Dan saw her and Nate embrace and was worried about the impression that she left on the young Humprey. Naruto could only raise his eyebrow at her when he heard the story but looked right back at his friend. "Serena just explain to him that it meant nothing and besides with the history that you and Nate have you should be worried about Blair and be honest with her." The redhead said to her with that Naruto got out of the shower and decided to get dressed and walk with Serena to the Brunch.

 _ **Back with Dan**_

His tasks were just about finished and he couldn't wait to get home to sit in front of the television to watch the classic movies marathon. Working for Eleanor Waldorf was no easy task and no task that you could put a set time in which you'd be finished so what he thought would be a quick and easy thing heading in earlier this morning ended up taking him longer than anticipated. As he was getting ready to leave for the day, he noticed Darota struggling with a few of the last-minute presents that she was supposed to take to the brunch as a token from Eleanor herself to the board members of Bass Industry. It was always an amazement to him how much they all intertwined in each other's world, Eleanor designing dresses for Chuck's father's board members, it seemed like the stuff you'd hear off of a movie or something he thought to himself. He couldn't exactly rush out on Darota and pretend like he didn't notice her struggling so being the gentlemen he had yet to be thanked for, he helped Darota out by assisting her to the brunch at the Palace. When he had first walked in it didn't really dawn on him where he was until he saw all the lavishness that went into just a simple brunch. Putting the gift boxes down on a special table, Dan prepared to leave but had accidentally bumped into a familiar face.

"Sorry…." Dan apologized before he realized who it was "Serena" he shook his head as he also saw Naruto with her "You would be here because this is…I should go" he said before Serena stopped him.

"No, I wanted to talk to you actually," Serena told him.

"Me or use me to talk to Nate?" Dan asked.

"I guess that's fair. Look, I never meant to use you or anything like that" Serena replied.

"You invited me to a party and then I caught with someone else," Dan said being discreet knowing that this bit of information couldn't get out at least from him

"And I'm sorry about that. It was a mistake, and I would really like to make it up to you" Serena said.

"Me? I'm the last person you need to worry about. I think the fact that the person you were with, is the same person that is with your so-called best friend…I think she comes before me in the list of who you need to make it up to" Dan replied.

"I know," Serena said "But last night, I really did want to hang out with you," she said with sincerity in her voice.

"I find that hard to believe since you never were around, and when you were you always had to go do something…so I find your admission of wanting to hang out with me a bit false" Dan said.

"It was a mistake, and I don't like Nate in that way. I was just caught up and did something very stupid, but I don't want to be that person you think I am" Serena said.

"I use to think a lot about you…you know, in a good manner. After last night, I can't help but think maybe I was wrong" Dan said before his glanced up to see Jenny "What the hell" he then said to himself

"Just give me a chance to make this right" Serena said

"I…I….my sister," Dan said as Naruto too saw Jenny wondering why she was there.

"What about your sister?" Serena asked noticing his eyes were focused over at Jenny who was soon joined by Blair "Your sister and….Blair" she replied finding it a bit odd that Blair was now buddy-buddy with a Humphrey of all people. Unable to take the sight of Jenny and Blair together just for the simple fact that his little sister could possibly be infected by Blair Waldorf, Dan had to figure out what the hell was going on. Making a mad dash over towards them, he could quickly see that Blair was relishing an angrier side to him.

"Humphrey, what are you doing here?" Blair asked with a surprise in her voice.

"Question is, what is she doing here?" Dan asked as he looked to his sister

"You never told me you had a sister. Jenny and I ran into each other, got talking and now we're here" Blair replied.

"I thought you were visiting then going home?" Dan turned to ask Jenny

"I did, but like Blair said we ran into each other. Why can't I be here? You're here" Jenny said

"Because I was doing my job, now that it's complete, I'm leaving," Dan said "You should leave now as well," he said

"Stop being so uptight Humphrey. It's just brunch" Blair sighed as she locked eyes on Serena and Naruto as she waves to him and not her.

"Stay here, and don't do anything," Dan said before he pulled Blair off to the side.

"Let go of me!" Blair declared as she hit Dan on the arm. "What are doing? I don't want my sister here" Dan told her.

"Frankly, I don't care what you want. So get over yourself" Blair said before they both glanced over to see Chuck make his way over towards the giddy blonde "Seems like she's already making friends" she then laughed as she could see steam coming from Dan at the sight of Chuck and Jenny "Welcome to my world Humphrey, strap up, its going to be a bumpy ride" she said as she walked away leaving Dan to wonder what she meant by that statement

"What the hell are you up to Waldorf?" Dan asked himself as he looked on quizzically.

After a few moments of making nice with a few of her mother's clients, and playing up the supportive girlfriend for Nate's fathers' clients, it was enough to make Blair feel detached from everything in general. Although she had gathered enough information to destroy Serena, she still felt like the true fool in this scenario was still her. Of course, torturing Dan with the possibility of her ruining Jenny made her laugh a bit, but even that wasn't enough to shake the feeling she had. Looking over at Chuck trying to deflower his virgin was as sickening to the core, how desperate was he, she thought to herself. Feeling as if she needed to get away, Blair made her way upstairs to Chuck's suite for a drink. Making her way off the elevator, she felt a bit at ease to know that in a few moments she would be able to numb the pain a bit with a much-desired drink as she entered into the suite and quickly poured herself a drink. Letting the sting of the drink linger a bit on her tongue, Blair gripped on tight to the glass as she just closed her eyes wishing this wasn't her reality. Before she had the chance to fully succumb to her emotions in a quiet but still way, she heard her name being called out by a familiar voice. In that instant, she was forced back into her hell as Serena came into the suite looking more pathetic than ever to her.

"What do you want?" Blair asked coldly.

"You've ignored me. I thought we should talk" Serena replied.

"There really isn't anything to talk about," Blair said "I mean what's done is done, and frankly I'm over it," she told her before taking another sip of her drink

"Will you just let me explain?" Serena asked

"What is there to explain? You crossed the line. You can't spin this one" Blair yelled at her

"It was a mistake, but I never…" Serena cried before Blair cut her off knowing the cliché line that she was about to say

"Never meant to hurt you!" Blair replied angrily "Newsflash, I'm hurt" she the shouted at her

"What can I do? What can I do to make this up to you?" Serena asked

"Leave. Never come back, that would be a start" Blair sneered at her coldly "Everyone was better off without you here. Hell, your mom was actually leading a normal life until you showed up" she said

"You want me gone? That's not going to solve things" Serena replied

"You have no idea how much it would solve" Blair said "I mean things were perfect until you came roaring back into town" she said

"I'm not the same person. I've changed" Serena said

"Spare me, your still the same person crap. I've heard it so many times and it ends in the same result" Blair told her as tears welled up in her eyes "I just….I just never thought you'd betray me like that" she said to Serena, making her feel guiltier by the moment

"I never meant to, its just one thing lead to another and I was drunk….then it just happened," Serena said as a bit of confusion came to Blair in that moment

"One thing leads to another?" Blair said softly as Serena kept babbling on in between tears.

"I never meant to have sex with him" Serena finally said and that was it. That was the confirmation upon confirmation that Blair heard that just made her

"You….you. You slept with him?" Blair asked in confusion as she laughed at how things just got worse by the minute "You and Nate had sex" she said just motionless

"I thought….B, I…" Serena said as Blair just put her hand up for her to just stop

"We're done" Blair breathed one last time before she quickly opened the door to see Nate about to knock

"Hey," Nate said as Blair just looked even more horrified "Blair, what's wrong?" he asked before she just ran passed him and over to the elevator.

"B, wait" Serena called out as she raced after her friend but she had already got on the elevator.

"What happened?" Nate asked as Serena hit against the elevator buttons in an effort to catch up with Blair.

"She knows," Serena said.

"Dan told her?" Nate asked as he was really pissed off about the fact.

"I did, by mistake," Serena said before the elevator doors opened and they both got on.

Becoming more and more irritated by the second, Dan clenched his fist tight as he looked on at Chuck and Jenny just laughing and flirting with each other. He always knew that his sister would eventually date, and he had more than like some of the guys she had crushed on, but Chuck Bass. The guy was a creep just by appearance, he may have been draped in designer clothing from polo's to designer dress shirts but he was still a creep. Images of what Chuck attempted to do to a drunken Waldorf paraded his mind as not even small talk with people, who just wanted to inquire information about the help took his eyes away from the pair. Extending his hand to rest on her shoulder, Dan did his best to keep his cool but it was when Chuck's hand had traveled further down onto her butt is when Dan just couldn't hold it any longer. It felt as if he was nearly sprinting a mile over towards the two as he made his way over to interrupt, but he was more than ready to yank his sister out of here if need be and by how Jenny was acting…it might have come down to it.

"Okay, grab your stuff. We're leaving" Dan told Jenny as he grabbed on to her arm

"Dan?" Jenny asked in disbelief

"Leave the lady alone" Chuck replied as he shoved Dan off of Jenny.

"The lady is my sister!" Dan yelled at him as Chuck just smiled at the thought of corrupting the very girl that happens to be Dan Humphrey's sister.

"You don't say" Chuck laughed as Dan looked on to see Katy and Isabel texting a mile a minute.

"Yeah, I do and she's coming with me," Dan said before he reached for Jenny's arm but she had pulled away.

"I'm not going" Jenny replied just as Blair came racing down the stairs with Serena and Nate not too far behind.

"Blair, will you stop please!" Serena called after her friend.

"Jenny lets go," Dan said grabbing on to her arm.

"No, Dan!" Jenny replied as Chuck once again stepped in

"Okay, you're taking this whole chivalry a bit too far now. If she wants to stay then she stays" Chuck said to him as all the attention in the room turned towards the group

"Have fun with some other random chick, but the girl, my sister, is leaving right now. Jenny grab your stuff!" Dan forcefully told her before Chuck grabbed ahold of Dan by his shirt catching Blair's attention as she soon saw how things were escalating.

"We have unfinished business, so do yourself a favor a leave" Chuck whispered forcefully in his ear as Dan tried to shove him off of him.

"Chuck, leave him alone" Serena yelled at Chuck as she looked on at the two.

"Poor devil, so little time so many sluts to fu…" Chuck managed to say before Dan pushed him off and then punched him. In one motion, that's all it took for every person in the Upper Eastside to know what had just gone down as he could hear the whispers explode within the room

"Jenny, grab your stuff," Dan said soft enough for Jenny to here.

"You weren't happy until you had to embarrass me" Jenny shouted at him as she grabbed her things angrily before she stormed out of the room knowing that their every move was being watched as Dan and Jenny left.

"Darota, have the driver bring the car around…I'm leaving" Blair said to Darota as Serena once again tried to plead to Blair

"B, listen to me," Serena said

"I'm done. I'm done" Blair said pushing past Serena and out into the lobby of the Palace leaving both Nate and Serena behind.

Stepping outside to the sidewalk, Blair pulled out her cell phone and quickly went to her media section on the phone to begin playing back the video. The video in which showed Dan punching Chuck. She had accomplished what she set out to do, all with the help of Chuck's disgusting manner…she had accomplished her goal, but yet, in the end, …she was the fool.

Naruto saw all this could only shake his head in disapproval but he only smirks. Chuck was still nursing his face the redhead decided to give Chuck a drink to which the rich snob thanked but his insides were screw up as he had to run towards the bathroom in a rush. This only made the red-haired prankster to laugh at Chuck reaction. Naruto decided to it was time to go as he felt this party was sort of dead.

 **Back with Dan**

Pushing the door open in full force, Jenny stormed into the loft and into her room in a hurry as she began to throw her stuff down on the bed. Coming in a few steps behind her with no care of her being upset and throwing a temper tantrum, Dan felt a bit at ease that Jenny was out of Chuck's grasp but he began to fear the toll of his actions on his job. He knew word would travel quickly and that by the time he would wake up in the morning everything would pretty much be signed, sealed, and delivered. Letting Jenny blow off steam for a bit in her room as she grunted and groaned at his actions but he knew with the time that she would cool down and then get over it. It was about ten minutes in before she had finally calmed down and was sitting on the edge of her bed by the time he went into her room. He didn't say much at first but just stood there in silence as they both tried to think calm and collectively about what they both wanted to say.

"You should have told me," Dan said breaking the silence.

"Your not dad, I don't have to tell you my every move" Jenny replied.

"I told you this morning about what that world is like, I specifically made it clear about that world, and you just enter into woefully" Dan lectured

"Dan!" Jenny yelled at him

"Jenny!" Dan yelled right back

"What is so wrong about wanting to be a part of that world?" Jenny asked

"Because we don't belong in that world," Dan said "Believe me when I tell you that its not a bad thing to be from Brooklyn," he said

"For you" Jenny replied "I want to fit in Dan, and I don't know if you noticed or not, but fitting in with the girls at my school basically consists of designers and attending all the parties," she said

"And that's not you" Dan replied

"That's what you want me to be" Jenny replied "I'm not a kid anymore…" she said before he cut her off.

"If you say you're a woman, I will projectile vomit on you," Dan said.

"I want to try different things. I want to explore more than just Brooklyn" Jenny said.

"So you let some jackass like Chuck Bass hit on you, that's as different as you can get there," Dan told her.

"It's my life, Dan!" Jenny replied.

"Not until your eighteen, it's not your life just yet…you just rent it until you get full ownership at age eighteen" Dan replied as he pulled his keys out.

"Where are you going?" Jenny asked.

"Out" Dan replied as Jenny reached over to grab her coat.

"I'm going to call Chuck," Jenny said.

"No, you're not" Dan laughed at her.

"Says who?" Jenny asked just as Rufus made his way inside of the house with groceries in hand

"Jenny. Dan. I got food. I'm in the mood to make a messy pizza" Rufus said happily as they both just looked on at their father but Dan had a bit of a wider smile knowing that Jenny's plan had been interrupted

"Yeah, after I don't think you'll be leaving any time soon" Dan laughed as he walked over to the door to leave

"Where are you going?" Rufus asked

"I have to go back to work to finish up work, I'll be back in two hours," Dan said before he opened up the door and left

"I hate my life," Jenny said to herself as she just watched her brother walk out like it was nothing

The light from city shined through the darkness of her room as she just lay in her bed staring up at the ceiling. In a span of three days, Serena van der Woodsen had come in a destroyed all that was perfect in her world. All that she had proud of, she had the perfect boyfriend, she had her minions, and she was Queen of it all…but now, all she wondered is what Serena would take next. It had been five minutes since she hadn't heard her phone vibrate, which all fifteen times was Nate probably wanting to tell her sorry a million and one times, and a part of her felt a little relieved to finally just be able to think, think about her next move, just think in general. A single teardrop rolled down her eye as she just thought about the day, wondering if the one success she had was really a success compared to the burned that she had received by the two people she cared for the most in this world. Sitting up in her bed, she once again looked on at the darkness in her room feeling as if this feeling would only continue, it had always been this way in the shadows of Serena. Getting up from her bed, she reached over to take a sip from her glass of water before pressing it up against her chest as the tears continued to fall. Lost in the sadness of the moment, she heard a knock at the door.

"Go away," Blair said softly as she pressed her hand up to her cheek to stop the running teardrop."We need to talk" Dan said as he leaned up against the door

"I don't want to talk to you!" Blair yelled

"Look, I don't care about your temper tantrum because you're going to listen. I don't know how you know Jenny or why you're all of the sudden talking to her, but if it has anything to do with me…keep her out of it" Dan said

"Leave. Me. Alone!" Blair screamed as she threw her glass at the window

"Glad to see we understand each other" Dan said after a moment of silence came between them. Heading downstairs, Dan heard the elevator doors open and as he made it to the final step he saw Nate come in.

"Hey man" Nate sighed

"Not tonight" Dan replied leaving Nate confused

"I have to talk to her. If we talk then things will be fine" Nate said

"Yeah, for your sake it'll be fine, but for her sake…give her time" Dan told him "Look, I don't know what the history is between Serena and you, but be honest with her because she seems to care a lot about you and all I see, is that you don't feel the same about her" he said

"I love her…I love both of them" Nate admitted "I can't just walk away from her" he sighed

"You can, and you will," Dan said as he extended his arms out so he was grabbing the rails of the staircase so that Nate couldn't get past him

"What are you doing?" Nate asked

"I'm considering here," Dan said motioning up to Blair's room "I should have done it earlier, but I'm doing it now. So give her space" he said as Nate with much thought then turned around to leave. As Nate went down he saw Naruto wondering why was he there but he needed the distraction.

 **So what does our Favorite Fox want with Nate seems like it must be important?**

 **Xoxo - Gossip Girl**

* * *

 **Author notes**

So here the thing I rather make Naruto have red-haired because his Mom had red hair and most of the other Uzumaki's did too. He still has his whiskers and blue eyes but i reincarnated him meaning he would still look the same but DNA is still DNA and i made it so his Mother's hair went into his instead of Minato's. Some of yall are complaining this is not the Naruto we love he doesn't have his signature blond hair. But there are some other stories with a red-haired Naruto and i don't need to get attacked for it. If you don't like my story and make a story yourself because i put my heart and imagination and my knowledge of a show i watched. The next crossover i wanted to do was a Naruto and A Two and a Half men or a How i meet your Mother. If some of you want me to do either of those or have some ideas you want to run leave a comment or Pm me. Also, I'm going to update my Naruto Shameless crossover so watch out for that.


	4. Chapter 4

**Chapter 4**

From last night Nate and Naruto were faced to face. "So is there anything i can help you with exactly?" As the brunette was wondering why Naruto was even here but for some reason, he felt sleepy as he thought he saw Naruto's eye change but that seemed impossible. Naruto only smirked as he took Nate sleepy body somewhere but he didn't want to get rid of it so instead, he decided to prank him.

 **Next Morning**

Finally reaching the level of perfection that was necessary for the Queen Bee status, topping off the product she had become of perfection, she reached over to grab her headband. Slow with anticipation, she brought the headband to her head before slowly putting it on. Fixing up her hair a bit she gave herself the final look over as she was now ready to show the public the style that she possessed. Stepping out of her restroom she was greeted by Darota with her Chanel bag fully loaded with the necessary primping requirements, along with her blackberry filled with the necessary contact list that would get her the much-needed information. Reaching in her purse, she grabbed her lip gloss and applied before she made her way over to the door.

* * *

 ** _Gossip Girl: There's plenty of upside to being the spawn of the fabulously wealthy, but the downside, super successful parents expect nothing less from their offspring and when it comes to college that means the Ivy's. It's more than just getting into college, it's setting a course for the rest of your life and for those few who aren't legacies, the pressures are no less. When parents have sacrificed for their children's future, what kid would want to let them down?_**

* * *

Sitting at the table, she sat with her plate in front of her just texting away while the staff looked on to see if the meal was to her delight. Standing with their hands folded behind their back, Blair just sat there not caring as to who or what they desired to hear from her about their services. Putting her phone down on the table, she looked on at all eyes fixated on her just feeling as if she was more than pressured to eat her food. To oblige the staff she took a single bite of her eggs before she put her fork down then walked away from the table. As she walked down the hallway she heard a bit of grumbling come from within the dining area. Hearing the sound of the fax machine going off, a slight but irritating smile came to her face as she slowly opened the door to her mother's office to see her going through her paperwork. Her mother hadn't torn her attention away from her set out the task, which allowed her the time to get comfortable in the seat in front of her mother's desk that way she could show that she was purely about business and well being as opposed to personal vendetta's. Glancing up, Eleanor was a bit surprised to see that her daughter was in her office and not off at school.

"I thought you'd be off to school by now," Eleanor said as she continued to look for her paperwork.

"I have ten minutes to spare before the driver comes. I'm glad that you've…misplaced something because it'll give us the opportunity to talk" Blair replied

"By talk you mean you complaining," Eleanor said.

"If you want to put it that way, I call it an update on staff relations," Blair said as Eleanor leaned back in her chair letting out a sigh.

"Do you ever think of making nice with the people that cook for you, steam your clothes…" Eleanor began to list before Blair interrupted

"All stuff that they're paid to do. Mother, we can't just let the staff run amuck" Blair said "Haven't you heard of Julius Cesar?" she asked

"Blair, get on with it. I have back to back meetings today, then I have to fly out to Milan tonight" Eleanor told her

"You're not going to be home tonight?" Blair asked sadly

"If you take this long then I will be, but no, I will not be back until this weekend" Eleanor replied "So get on with it? What is this staff relation you feel I need to know about?" she asked as Blair pulled up the video of Humphrey punching Chuck on her phone to show her mother

"I think this is enough evidence to show that he's not qualified. A woman of your stature doesn't need him as representation at events that we are both well known at, I mean this could have seriously affected my standings in the social circle" Blair stated as Eleanor pulled out her glasses to look on closely at the video

"What am I watching? It looks like two blots moving…one blot, in particular, has bright clothing that no man should ever wear" Eleanor commented as she squinted on at the images

"It's Humphrey punching Chuck" Blair declared to her mother.

"Why is Daniel punching Chuck?" Eleanor asked as she continued to squint.

"I don't know, call it the inner hood in him coming out for all I know. That right there is grounds for termination" Blair said.

"Do you know how the fight got started?" Eleanor asked.

"I don't know. All I know and clearly feel is right under these circumstances is we change all the locks, maybe even double up on security because Lord knows what is being taught in the Bronx" Blair suggested.

"I'm not firing Daniel" Eleanor laughed.

"Why not? What more do you need?" Blair asked in disbelief.

"Does it ever occur to you that you should form a relationship with the people who work here? I mean a lot goes into working here" Eleanor said.

"Oh, spare me the charity case approach. I donate to NAACP each year, so I've more than helped the minority and I refuse to help some inner-city youth bamboozle you into thinking he's some noble character" Blair replied

"I'm not firing him, so you can just give it up to Blair" Eleanor sighed.

"What is it with him? I mean really? Why is he all of the sudden tugging at your heartstrings?" Blair asked as Eleanor took a moment to think

"He reminds me of your father" Eleanor smiled as Blair put her hand up in hopes that her mother wouldn't continue on

"Okay, please. Stop right there, if hiring Humphrey is to inspire some sort of sexual lust inside of you…then you really need to get some help" Blair replied

"This has nothing to do with sexual lust. Daniel looks as if he just needs an opportunity, and I fully intend to give that to him…maybe you should as well" Eleanor said before her cell phone began to vibrate "If you will, I have to take this…it's Tokyo" she told her daughter before Blair caught the hint that her presence was no longer necessary anymore.

* * *

 **With Dan**

Looking down at his class sheet as he came out of his second period, Dan began to rack his brain on where his next class would be with Professor Harmen for Political Science. Running his hand through his hair, he just retired the thought to be something he would deal with after brunch. Making his way over towards his locker, he quickly pulled his books out to put in his locker for the next days class as he attempted to lighten his load for travel at night after work. Still feeling a bit tired after he stayed up all night typing up his research paper that was due for his Advanced Placement classes, he was more than ready to hurry and get this day over with. Leaning his head into the locker finding the darkness within the locker a bit comforting with his sleep deprivation, he was soon torn away from his peaceful rest by the sound of someone clearing their throat. At first, he didn't make much of it, but when he heard someone press up against the locker beside him along with the biting of an apple sound, that was enough for him to realize that maybe this person was trying to talk to him or wanted his attention. Closing the locker, Dan was a bit surprised to see the smug look on Carter Baizen face. Fanning away the spreading aroma of smoke that came from a cigarette that he held in his hand, Dan found his locker mate a bit odd.

"You do know your not suppose to smoke on school grounds, right?" Dan asked as he continued to fan away from the smoke

"You can when your parents donate thousands of dollars to the school. It's public domain" Carter declared as Dan looked around in hopes that no one saw him with the cigarette.

"Public domain is on the sidewalk, this school is private" Dan replied.

"Are you always so straight-laced?" Carter asked with a slight grin on his face before taking another drag from his cigarette "I mean you smell of…" he said as he began to sniff Dan causing Dan to feel an uncomfortable "A conscience. Oh, my God! This school has a conscience walking among them" he laughed with crazed abandonment

"Okay, and on that note, I will be leaving," Dan said as he closed his locker and began to walk away but Carter only followed behind until he caught up with him

"The name is Carter. Carter Baizen" Carter introduced himself as he held his hand out for Dan to shake

"Nice to meet you, I guess" Dan shrugged "Look is there any way that we could separate, I would kind of like to fit in at this school," he said

"Don't fit in, be abstract from that. Fitting in will morph you into one of them, and you strike me as a person that isn't the least bit interested in being like them" Carter said as he pointed on at their classmates

"I guess you'd be right," Dan said before he took a seat at one of the tables

"I know I'm right" Carter smiled "But I have come to rescue you from this hell hole that is the Upper Eastside," he said.

"I'm perfectly fine by myself," Dan said.

"Daniel, you're in denial" Carter laughed.

"How do you know my name?" Dan asked in confusion just as Serena made her way over towards him and Carter with books in hand as she took a seat at their table

"Hey, Dan" Serena smiled "Carter" she then greeted with a smile

"Serena van der Woodsen, that's how I know you. We shall talk later" Carter said patting him on his shoulder before he got up

"I rather we don't" Dan sighed

"Remember, I'm your guide. You'll thank me later" Carter said before leaving the two

"How have you been?" Serena asked

"Uh, busy. I have been busy" Dan replied "You?" he then asked

"I have been surviving, if that's an event the word for it" Serena replied to his question with a bit of sadness "Blair won't take my phone calls or answer my texts hence leading me to the conclusion that she is still upset with me," she said.

"Can you blame her, you kissed her boyfriend" Dan replied as Serena found it a bit interesting that he hadn't heard the full story yet.

"Yeah, I kissed Nate" Serena replied strangely "But I guess I could add busy to the list with everything with my brother," she said

"What about your brother?" Dan asked "I didn't even know you had a brother," he said

"A little brother, to be exact" Serena smiled "He's…he's in rehab. The Ostroff center" she replied nervously

"Oh, I'm sorry" Dan apologized

"No, need. Every family has their issues, but with the added tension with Blair…it doesn't help" Serena sighed "Has she mentioned anything to you?" she asked

"Me. Blair. Talking. Yeah, I think that's something that doesn't happen due to the laws of nature and if it were up to her, social standards to live by" Dan replied.

"You work for her though?" Serena asked.

"I work for Eleanor, not Blair" Dan corrected "So whatever progress she is making back to your estranged friendship, I would know nothing about" he then said as he looked over across the courtyard to see Blair with her minions grading the incoming class of freshmen. Rolling his eyes at her need to exact her power on those, who are just terrified if they can't find their class much less not possessing the latest bag from Marc Jacobs.

"And us? What progress are we making?" Serena asked before the school carrier came over to him with a pink note in hand to give to Dan "What is that?" she asked as Dan read the note

"The headmistress wants to see me" Dan replied a little confused as he looked on at the note.

Before Dan left Serena wanted to ask him one more question. " Have you seen Naruto I haven't seen him all morning." The It Girl asked as Dan only shooked his head as he had not seen the red-head leaving Serena alone to her thoughts as Dan left.

* * *

It was all ready the first day and she was being called in by the headmistress, could this be that she was finally acknowledging the twenty letters of her college application she had sent over the summer. No, if there was going to be anyone in charge of her fate for Yale, Blair was determined for it to be up to her and not some headmistress with a salary that could barely afford a lobster with the steak at the finest of restaurants New York had to offer. Though she did feel a bit thankful that she had been pulled away from freshmen intake, which was basically the judging of the crop to see who could even make it on to the waiting list of the waiting list to be one of the girls of the steps. Each day, Blair and her minions had lunch on the steps of the Met as some sort preservation of the great beauties, the Met created masterpiece after masterpiece…so it was no shock that Blair felt the need to be surrounded by such creative genius by the many that graced the halls of the met, which is why it was no easy task to be one of those girls. This required rigorous tutelage from her and whatever thought her minions could muster up. Approaching the headmistress's office, Blair began to fix herself up before she entered the office to find that she was all readily expected. Lead to her office by the secretary, Blair forced the biggest of smiles on to her face before it quickly faded once she saw Humphrey sitting in a chair in front of the Headmistresses desk.

"What are you doing here?" Blair turned to ask him

"Hello to you to Waldorf," Dan said forcing a smile as he didn't like the idea of being in the same room as her as much as she didn't

"Blair, take a seat" The Headmistress instructed her as she did as told reluctantly

"Shouldn't the headmaster be in charge of the boys, hence the term headmaster?" Blair asked

"He's out on sick leave, apparently Vegas and fallacious women can do that to you in the city of sin" The Headmistress replied

"Isn't the Headmaster your…oh, never mind" Dan said realizing that it was a sore subject to bring up seeing as the previous statement had said so much all ready

"I hardly doubt that Humphrey and I would have anything in common that would require both of our presence in here," Blair said "I mean I thought we were going to discuss my college letters to Yale. I see no need for me to be present for his questions on applying for financial aid, though I always urge my esteemed parents to always help those who are less fortunate" she said

"Do you even have a nice bone in your body?" Dan turned to ask her.

"I'm stating a fact. Fact, your not on the same level as me Humphrey. Fact, I find my time at this school valuable in my future endeavors" Blair said under her breath as the Headmistress just listened in on their banter

"That's not fact, that's being an egotistical maniac" Dan scoffed at her notions of what was fact "And I do happen to be smart," he said.

"You heard that, right? I mean grammar mistakes after grammar mistakes….and I do happen to be smart" Blair quoted him towards the end "How was he even allowed an application for St. Jude's, I'm outraged that my tax dollars are supporting this walking fragment" she said

"Okay, I've heard enough" The Headmistress said before she took a sip of her coffee "If you two can manage to bite your tongues for a mere ten minutes, then I might be able to accomplish more than finding a divorce attorney on my list of things to do today" she said "Now as you both know, it has been a long-standing tradition for us to have an Ivy Week" she told them.

"A tradition I come to admire" Blair smiled.

"The Constance Billard girls will be in charge of Friday's night mixer, while the St. Jude's boys will provide ushers for the Ivy representatives," The Headmistress said as Dan began to perk up.

"Yes, a position in which I applied for…Dartmouth's representative to be exact" Dan replied as Blair laughed to herself.

"That's a tall tale" Blair replied.

"Laugh all you want, but there is a reason for Mr. Humphrey to be here Ms. Waldorf" The Headmistress replied.

"To be a thorn in my side is one reason. I still don't get why we're both here?…that's the part that leaves me in anticipation" Blair said

"I'm sure if you were to refrain from all that is you, you would soon find out," Dan said to himself as Blair just glared over at his direction while he played with his tie

"You two hold the highest grade point average in your respective division of schools. Blair for Constance and Daniel for St. Jude's" The Headmistress said "Which is why we would like for you two, by the grace of God, to work together to put together the luncheon for Saturday" she said

"Work together?" Blair asked "Can't this be divided into tasks for Constance and St. Jude's?" she asked

"Yeah, I mean I'm already up to my eyeballs on exams, work, then impressing Dartmouth" Dan chimed in

"For both of you, who are dreaming to attend an Ivy League, this luncheon is the most important focus" The Headmistress

"I'm sorry…are you encouraging me to just put all my focus on this one luncheon that I have to plan with….put together over my studies?" Dan asked

"Precisely, but it's not pressuring" The Headmistress smiled "Look, I do not doubt that you two will somehow work this out, as well as, tend to your studies," she said "This is something to be expected from you both. This is your dream and this is your opportunity" she then pointed out.

"And the usher positions, am I automatically taken out of the running?" Dan asked

"Yes, but if this luncheon is the success I know it will be then you'll be memorable in other ways that will matter," The Headmistress said as Blair began to daydream about all the possibilities this could lead to as she'd have one more added bonus of extracurricular to put on her resume for Yale.

 ** _[Flashback]_**

 ** _Descending the staircase with the biggest of smiles plastered on her face, Blair was overjoyed with the happiness of thoughts of Yale. She had finished up reading the latest updates to the campus and she found the yearning thirst for knowledge was only increasing by the minute on the campus, and she someday would be a part of that great tradition that her father spoke so highly about. Joining Darota in the living room area, she sat on the sofa still in midst of a daydream while Darota just continued on with her daily tasks._**

 ** _"Do you remember when Dad gave me my first Yale sweatshirt? I don't think any piece of clothing has ever fit me more perfect, not to mention how adorable I found that bulldog" Blair smiled at the not so distant memories while Darota just looked on at the brunette with concern that she may have become delusional "Remember when I asked you if I could get a bulldog? Good call, by the way, saying no… and now the big day is finally here. Soon Nate and I will be at college, him going down to Yale, me going up to Dartmouth. Dad flying in for the Princeton game, I hope it doesn't make you feel old watching me grow up"_**

 ** _"Eat up Ms. Blair" Darota encouraged her as Blair leaned forward to grab a single grape to put into her mouth to oblige Darota's wish_**

 ** _"Finished" Blair replied before she rose from her seat_**

 ** _[End of Flashback]_**

A smile slowly came to her face as she began to realize that this was going to be her moment, her moment to seize the opportunity and maybe, just maybe put her life back on the path it was supposed to be on. Noticing the devilish smile that his peer wore on her face, Dan could only hope that was a sign that she would work with him. "We won't let you down," Blair told the Headmistress before she rose from her seat to give the headmistress her million-dollar smile before turning to leave. Unsure as to what this meant, Dan nervously made his way out of the office to follow behind Blair into the hallway

"So are we doing this?" Dan asked her as he trailed behind her as she texted away on her cell phone, not giving him any attention "Waldorf. Waldorf. Waldorf!" he called out before she slowly turned towards him.

"Will you lower your voice" Blair instructed "There is no we in this, all that is expected of you is to just smile and no if you can do that at the same time then great but stay out of my way on this one Humphrey?" she said.

"Oh, no," Dan said before he ran in front of her "Your not going rogue on me, we're doing this together," he said.

"Get out of my way Humphrey," Blair told him calmly.

"Not until you agree that we will work on this together" Dan replied with determination in his eyes.

"I'm giving you Dartmouth on a platter, just go with it" Blair replied.

"I don't need you to give me anything, I've worked my butt off for this opportunity and I'm going to get it…not you. So do we have an understanding?" Dan asked her once again as she returned to texting on her phone "I do know where you live" he threatened.

"If your trying to sound like a stalker, ding ding ding, you've accomplished it" Blair replied "Fine. I will allow you to prove that you're not as dumb as you look" she sighed."Thank you. I think" Dan replied unsure if that was a semi-compliment.

* * *

Standing amongst her minions, engaging in the latest of gossip about the freshmen intake, Blair found physical education a bit more bearable with gossip involved. Even with the task of putting on a prestigious event for Ivy Week, there was never a shortage of what she had to do to keep order in line. Laughter filled within the circle as they poked fun at the not so appealing gym attire the newbies had to wear as opposed to their gym chic looks that took them all but one day to master in their stint at Constance, but the laughter had soon died down as Serena made her way out on to the field with her field hockey stick in hand.

Isabel and Katy began to whisper amongst the girls, informing them of the all ready cliché rumors that had come along with Serena by this point as Blair became irritated with even hearing Serena's 's glare quickly came upon the blonde, who did her best to play the victim, but there was no way that Blair was going to let Serena fool people into letting them think she was the one done wrong. Things were still pretty much fractured between Nate, but she had hoped with enough time for him to realize that he made a very stupid mistake that they could work things out and come back stronger than ever…sort of like Nicole Kidman and Keith Urban she thought to herself. The teacher quickly gathered the girls in the middle of the field and instructed them as to what positions they would play, and Blair began to relish the feel of a stick in her hand and the possible ways she could make Serena pay for the embarrassment she had to endure. Placing the ball in the middle of the circle, the game had just begun. Both Blair and Serena ran after the ball as Serena's quickness had allowed her greater advantage. Struggling over the ball, Serena quickly began to feel as if Blair was going after more than just the ball.

"Look, I made a mistake with Nate okay" Serena tried to reason during their struggle "We don't have to be friends…" she said before Blair whacked her with the hockey stick causing her to fall down on to the ground. Taking a moment to collect herself, Serena rose from the ground before she took her stick to hit the ground angrily while all Blair could do was smile at her cheap shot at the blonde.

"Waldorf?" The teacher asked wondering why she took such a cheap shot

"Sorry, slipped" Blair replied as she walked towards her spot on the field before the teacher turned her attention over to Serena.

"I'm fine" Serena declared.

"All right, let's keep it clean ladies," The teacher told them just as Serena walked past Blair

"I really wanna believe that was an accident," Serena told her.

"Then you must be delusional" Blair laughed to herself. Running over towards the ball, Serena began to bring the ball up that was until Blair ran up and jabbed her in the stomach. Nearly losing her breath from the blow, the teacher quickly raised a green card up against Blair.

"Waldorf, focus on the ball," The teacher said.

"Thank you" Serena praised the decision, "Oh, stop acting like you're the damn victim in this" Blair replied before she slowly backed away.

Now caught up in the heat of the action, the girls were playing an intense game that was going down to the wire. With Serena being the most skillful on her team, she handled the ball most of the time as she was nearly bringing her team back to win the game. Passing the ball to her, Serena in a mad sprint was able to surpass the defenders as she passed off to the girl beside her so she could advance further before getting the ball back. She was nearly inches away from where she had anticipated to pull the trigger and hit her spot in which she knew she'd be able to score. Cocking her stick back ready to fire, Serena was soon torn from her goal as she was upended into the air by none other than Blair. Letting out a growl of anger as she gripped the grass in between fingers.

"I'm running out of colors here Blair," The teacher told her as Serena quickly got up to get up in her face

"And I'm running out of patience" Serena replied "Enough, okay?" she asked in hopes that they would burry the Hatchett

"It's enough, when I say its enough" Blair said not backing down from Serena

"Girls, play the game…leave the catfights until after school" The teacher said as they both went back to their respective teams to resume play. Receiving the ball from a teammate, Blair turned up the field and focused in on the ball as she tried to keep control of the ball before Serena swiftly ran across the field and tackled her to the floor. "Girls, break it up!" he yelled on at the girls as they just continued to wrestle with each other on the floor while the other girls huddle around them

"Get off me!" Blair exclaimed as she began to tug at Serena's hair before Serena tugged away from her grip and got off of her

"So we've come to physical blows now?" Serena asked in disbelief "Could we please just call a truce" she suggested as Blair ran many thoughts through her head as to what she should do. There was no way that she was going to let Serena spin this to her advantage. Becoming limp in one of her legs, Blair screamed out in agony as the overwhelming pain became too much for her

"My leg!" Blair called out.

"Serena, you're out of here," The teacher said as he walked over to access the damage as Isobel and Katy helped their ailing friend

"I hope its broken" Serena muttered to Blair as she left the field.

* * *

 ** _Gossip Girl: Hey Upper East Siders. We hear that World War Three just broke out and it's wearing knee socks. Choose your side or run and hide. We have a feeling that this one is to die._**

* * *

Although today was a momentary success against Serena, Blair knew that she'd have to do more than fake limp her way through the rest of the day if she wanted to do maximum damage to Serena. There was no way that she could let Serena gain the sympathy of the school, and if she wanted to break the former it girl than she would have to use the information she had in her arsenal. Acquiring the needed information she needed to deliver the perfect outing of Serena and what better way to ruin her than to add her future along with it. Ever since they were little, she had always remembered her friends desire to attend Brown University…it was the only school that Serena would ever dream of going to even though she had less than average grades. If she was going to exact revenge then it had to come in the form of the luncheon, and it had to be soon or else she was going to explode with anger. Stepping off the elevator still dressed in her gym attire due to acting purposes, Blair rolled her eyes in irritation as Dan came out of the kitchen with a plate in hand as he stuffed his face with Darota close behind with a smile plastered on her face.

"Since when is the staff suppose to take snacks" Blair stated in annoyance as she made her way over to the living area

"Ms. Blair, you look a mess," Darota said as she rushed over to her

"It was no thanks to Serena. I tell you, she's unhinged in the head or something" Blair replied as Dan began to laugh to himself

"I heard about the throw down on the field" Dan laughed "Who knew you Blair Waldorf could fight," he said "You even scarred up your knuckles there a bit" he went on to notice

"Shouldn't you be working? Not stuffing your face?" Blair asked

"This is work. Your mother wanted us to try out the caterers that she had sent over for an upcoming party…this is house management" Dan said

"I'm sure" Blair replied in irritation as she set her phone down on the table

"So should we get started with our soirée, I've come up with a list of things we could feature in the panel," Dan told her as he pulled out his notebook

"Maybe you like to come home and sweat it out over homework, but I'm going to take a shower and get washed up because unlike you, I don't like to smell I just traveled through a Mongolian meat market" Blair told him "Darota, will you please put all my calls to voicemail and if any of my minions call then give them the usual time in which they should call under call back times" she then turned to tell Darota

"It amazes me how you multitask in being evil" Dan replied as he leaned back in his chair "Is there any possible way you could actually be civil to me and not treat me like I'm trash," he said.

"I really don't have the time, nor do I care what you feel….if you were smart then you would have picked up on that" Blair replied as she made her way over to the staircase

"I'm not going anywhere. I will be right here" Dan said.

"I don't doubt that" Blair replied as she knew the leech would be sitting in the same position when she returned as she heads up to her room.

"What a bi…no, no. I will not call her that even though she is it down to the bone" Dan said to himself not wanting to stoop down to degrading the brunette. Running his hand through his hair in frustration, he was soon torn away from his frustrations by the ringing of his cell phone. Pulling his cell phone out, he looked on to see that it was Jenny calling him "Yeah, hey Jen" he said answering the phone.

"Are you at Blair's?" Jenny asked.

"Yes, I'm in hell to be exact but yes, I'm at Blair's" Dan sighed "What's up?" he then asked.

"Well I don't want to sound too happy, but I am," Jenny said happily "I made it past the first round" she declared.

"First round of what?" Dan asked.

"Of freshmen intake," Jenny said.

"Okay, I'll pretend to know what that means" Dan sighed as he looked on to see Blair's cell phone vibrating on the table. Getting up from the table, he reached over to grab the cell phone to take up to Darota but when he looked on to see that the Ostroff center was calling. "Jen, I'll call you back," he said before he hung up the phone while looking around to see that he was alone before he answered Blair's phone "Hello" he answered

* * *

Looking on strangely at her phone after her brother's sudden hang up on her, finally concluding to herself that maybe it was just as well that they stopped talking seeing as she only had an only a limited amount of time before she had to catch the bus. Making her way inside the center, Jenny signed in with the nurse then made her way over to Eric's room. Taking a seat on the edge of his bed, Jenny reached over to his nightstand to look through one of the gaming magazines that he had subscribed to during his stay here. Taking a glance at her watch she had known exactly what he was probably finishing up his final evaluation. She was thrilled that she was finally going to have her friend back at school, although they had met in class she had come to really enjoy her time with him over the past couple of months. Growing more and more concerned about the video games that were being featured in the magazine as all of them consisted of gory images that she felt might not be suitable for him. Just as she got caught in the mess that was his magazine, Eric had made his way into the room surprised to see her.

"I wasn't expecting you so early" Eric smiled as he walked over to hug her.

"I told you I was going to come by and tell you all about my day. How was your session?" Jenny asked

"I'd rather hear about school, that's how it was" Eric replied as he flopped down on his bed.

"That bad?" Jenny asked as she laughed.

"Yes. I believe that this was the worst one to date" Eric sighed "But seeing you here has made up for the crap fest that has been my day" he said

"Well, I do tend to give good company" Jenny smiled "So I've officially made it past freshmen intake, at least the first round," she told him.

"Freshmen intake? Wait you were actually serious about the whole Blair Waldorf thing?" Eric asked "I never pegged you as a Blair Waldorf type," he said

"What exactly is a Blair Waldorf type?" Jenny asked

"Basically rising from the level of freshmen to one of her minions. Do you really want that?" Eric asked

"I want to fit in. It's easy for you to criticize her because you've practically been around her your whole life, but I like her…I think she has some endearing qualities" Jenny said.

"Yes, Blair does have her moments. I'm not going to say that I hate her, I just think when your sister is best friends with her, and they are constantly best friends or frenemies…it gets kind of confusing at times about what you like about that person. I feel the same way about Serena, I mean she's back but in the back of my mind I'm wondering what now? What scandal is she going to be a part of next" Eric said

"Never thought that you'd dread your sisters return, I thought you two were close?" Jenny asked

"We were when we were little but as you can tell…as Serena's popularity grew the more detached she became from the family, and then my mom was always off at social events trying to maintain the family name even when Serena was wrecking it. I guess after a while you get used to things going bad in my family" Eric said

"Did your family have anything to do with you ending up in here?" Jenny asked

"I just got in a dark place," Eric said as he struggled to tell her

"You don't have to…I just, I guess we never really talked about you in that sense so I just was wondering" Jenny said

"No, it's fine. I think it might actually help if I talked about it with you" Eric smiled weakly at her "Jenny, I tried to…I tried to kill myself" he said.

"Why?" Jenny asked with a frown on her face not liking how Eric talked but she wanted to be there for her friend.

"Being in this world, it's a constant reminder of perfection and how you have to always be perfect. Problems aren't accepted. You can't wish for anything less only greater things. My mom was never really around, and Serena had her friends…so I had no one….until you and sometimes Naruto when he's not busy" Eric smiled.

"You should go to the luncheon with me" Jenny then suggested to him

"Okay, that was a weird segway. How did we go from talking about me to a luncheon?" Eric asked

"Because I think that you should get out of this depressing room, and take me out," Jenny told him

"Take you out, huh?" Eric smiled happily

"Yeah, everyone should hang out with friends" Jenny smiled before she reached over to mess up his hair "Now lets get you packed because I can't wait to come visit you without having to sign in….or do you have to do that at Palace still?" she asked

"No" Eric replied unable to hide his sadness "Friends are always welcome" he went on to say only driving the friendship dagger deeper into his heart while Jenny went on a rampage in his closet

* * *

Luckily throughout the week, Blair was able to find some trait in Humphrey that made him easy to work with, but she would never say that to him, let alone make him feel as if he was safe in her house. For the most part, everything was strategically planned for the luncheon and everything was locked and loaded for the ultimate reveal. With help from Isobel and Katy, Blair was able to get word on the fact that Serena was planning on attending the luncheon to talk with Brown representative about the possibilities of her going there. Of course, that small fact caused Blair a few good chuckles here and there because Serena's grades were barely even good enough to get into a regular university much less an ivy.

It always amazed her what type of logic Serena had to just think she could show up and be accepted just because she was Serena freak in van der Woodsen. Today, she'd prove that Serena was no better than the rest of them, once and for up in front of the school in her limo, Blair got out of the car with assistance from her driver to see Nate waiting for her in the courtyard. Apart of her wanted to ignore him but she knew that she just couldn't keep ditching him, eventually, they were going to have the talk. Slowly making her way over towards him, he leaned in to give her a kiss on the cheek before he pulled away.

"You look beautiful" Nate told her.

"Thank you" Blair replied, "I heard you got the usher position for Dartmouth, I'm sure you're excited about that" she then congratulated him.

"Not really, I mean its what my dad wanted" Nate sighed

"Your dad? Nate, you've always mentioned Dartmouth" Blair said

"Because of my dad," Nate said soon realizing that this conversation wasn't the best one for them to be having, especially when he was trying to make things right between them "I miss you" he then stated as she lowered her head to look away from his eyes

"I…" Blair began to say before she looked over to see Dan coming out into the corridor with Carter in tow "I miss you, too" she said tearing her attention away from Dan and back to Nate

"So then let's end this, let's start getting back to us" Nate suggested as he grabbed her hand to kiss "We should go away for the weekend" he then said

"Oh…any…any suggestions," Blair said as she looked over once again at Dan and Carter, who were then joined by the guy she had met at the Ostroff center earlier this week. Becoming alarmed, Blair pulled her hand away from Nate "I can't talk right now. I have…I forgot that I have to do a last-minute run-through" she said before she quickly made her way over towards Dan. Before she did leave Nate. "...Um, Nate, you have Clown make up on you i thought you should know" as she gave Nate a mirror before she left.

Nate looked at the mirror and could only think of one person capable of doing this and speak of the devil he had just entered the classroom. "Naruto I'm gonna kill you man, i hope this stuff is washable." Naruto had paid no mind to Nate as he went to sit down.

"Dan," Carter said as he motioned over towards Blair, who was coming up to them.

"Mr. Bryant, have you checked in yet?" Blair asked the man.

"I've already spoken to my group," Mr. Bryant said, "I'm highly impressed with this school" he went on to rave.

"Excuse me, what did you say? How did you already speak to a group? The program hasn't even started yet" Blair asked as she looked from Dan to Mr. Bryant."I might a last-minute adjustment," Dan told her "It was about making sure you have good mental health in order to succeed," he said

"Yeah, it was very riveting" Carter smiled on at Blair knowing that she was probably having a cow right now. "I really wish you would have told me about this?" Blair told Dan just trying not to do any physical harm to him before Nate walked over to join them.

"Carter. Dan" Nate greeted the two but the two started laughing at Nate's face so did everyone else but decided not to say anything.

"Nate Archibald, we've officially reached those we thought were unreachable" Carter laughed to himself.

"What's going on?" Nate asked Blair not obliging Carter's desire to start something with him.

"Nothing," Blair said before she grabbed on to Dan's arm "Can we talk partner?" she asked as he had no chance to reply as he was being tugged into the hallway

"Ouch!" Dan declared as he tried to pull away from her grip.

"You traitor!" Blair yelled at him before she hit him with her purse "You went behind my back and added things, after you specifically made a big deal about us working together" she said

"Only because you were going behind my back to screw over Serena" Dan replied as she looked at him with shock on her face "Yeah, I figured it out. The Ostroff center, really?…why would you invite them to Ivy Week" he said

"Oh, God! Does my whole have existence have to circle around Serena?" Blair asked "I invited Mr. Bryant for a special presentation," she said

"To embarrass Serena. He told me that you were asking about her visits and how often she frequented…I know everything" Dan said

"This isn't over. Not by a long shot Humphrey" Blair replied angrily at him "Serena thinks she can just come in and give her sorry's like its suppose to be big coming from her, well I'm tired of it!" she declared.

"And I get that" Dan said before she interrupted him.

"What do you know about it? I bet your one of the many people who fawn all over her….the only reason you did this was to make nice with her" Blair replied

"I did this to stop you from making a huge mistake" Dan replied.

"Oh, God. Spare me the PBS moment" Blair replied "In case you haven't noticed, on this side of town, things are cut-throat" she said

"Okay, so you do this. You embarrass Serena, how will that make you any different?" Dan asked her "What will you gain from this?" he asked

"Look, I don't expect you to get it on how things are, but stay out of my way or else I will destroy you," Blair told him

"You will regret this" Dan said.

"As will you," Blair said before she stormed off.

* * *

Nervously being lead through the group of people that gathered around at the luncheon, Eric began to feel as if he were an outsider making his way to the party for the first time. It had been enough to get eyes on him just because he was Serena van der Woodsen's little brother but ever since his attempt, he just felt in general that all eyes were on him. Looking back at her friend, Jenny smiled back at him hoping and trying to reassure him that things were going to be fine and that he was worrying for nothing. Stopping off at the appetizers they both grabbed something to munch on while they looked on at all the representatives that came from the different ivy leagues and the students that would have sold their souls just to attend their schools. Noticing her brother with a friend, Serena walked over towards Eric with the biggest of smiles on her face.

"Eric, you came" Serena smiled at her brother as she wrapped him up in a hug

"Yeah, uh…Jenny made me" Eric replied "Serena, this is Jenny Humphrey. Jenny, this is the great Serena van der Woodsen" he introduced the two

"Wait, are you Dan's sister?" Serena asked as soon she saw that her friend just came back from the principles office.

"Yes," Jenny smiled.

"Oh, well its finally nice to meet you. Eric tells me that he's got a friend, and I hung around late just to see this friend…so I'm glad to meet you" Serena said as Eric felt embarrassed.

"So have you talked with the Brown rep and Naruto did you get in trouble again?" Eric asked his sister and his friend.

"I have not. I've been waiting for the right time" Serena said "I get so nervous just going up to some rep and then relaying my life story" she said.

"The principle actually was laughing and just gave me a warning." The redhead stated

"I'm surprised you get nervous" Jenny replied.

"Big-time" Serena laughed "How are you feeling?" she asked wondering how her brother was dealing with his first day out.

"This makes me feel like I'm back in that room with that Brazilian woman, where she's asking me questions about Florida" Eric replied trying to feel comfortable as both Jenny and Serena laughed.

"I have a grandma that lives in Florida," Jenny thought off the top of her head as Eric just looked at her "In my head, it sounded comforting" she laughed.

"Has your brother made it yet?" Serena asked as both Naruto and Eric had both rolled their eyes,

"Uh…I haven't seen him since this morning" Jenny replied as they began to scan the crowd in search of Dan before Serena finally laid eyes on him and became excited to see him.

"There he is" Serena smiled as he walked up to them.

"Hey, Dan" Jenny smiled at him while Blair made her way through the crowd with Isobel and Katy right on her heels.

"Hey, I know this is going to sound weird, but I think you guys should go," Dan told them as this made all of them frown.

"Okay, that was weird. Dan this is Eric, Serena's brother" Jenny introduced Eric but found her brother's weird behavior a bit od.

"And we have reached the point of no return," Dan said to himself in hopes that they would understand and just flee "Serena, you have to go. All of you actually because…" he said before Serena cut him off

"Why do we have to go? What's wrong with you?" Serena asked with much concern for Dan

"Look, I can't explain but you should go" Dan warned them once again

"Eric, I'm sorry. My brother is acting crazier than usual" Jenny told him just before Blair grabbed the microphone

"What's wrong?" Serena asked again as Dan wore a look of defeat on his face before he turned to look at Blair up on the stage.

"Can I please have everyone's attention?" Blair said as everyone turned to the stage "Welcome again to Constance Billiards and St. Jude's luncheon. My name is Blair Waldorf, chair of the community outreach committee" she said as everyone began to clap for her except Dan as he knew what this was all leading to. Making his way towards the stage, Dan shook his head in disbelief that she was actually going to go through with this

"Who knew she was so involved" Jenny whispered to Eric

"You clearly don't know Blair then" Eric laughed.

"Every year our schools choose to support one local institution that we feel benefits our community. This year our schools have chosen to honor the Ostroff Centre" Blair revealed sending a nervous feeling through Eric's body as he looked around thinking that everyone's attention had turned towards him. Listening in intently as to where Blair was going with this, Serena couldn't help but notice that Eric was slowly becoming a nervous wreck but she was thankful that Jenny had grabbed onto his hand to cause some sort of relief. Looking down at their connected hands, Eric didn't know whether to feel like this was a moment between them or her showing support for him

"Blair!" Dan whispered loud enough so that she could hear, but she paid no attention to the boy on the side of the stage that was trying to catch her attention

"This year's choice is a very personal one because the center has helped one of our own." Blair smiled as all eyes began to look around to see who the lucky person was. Slowly getting a clue as to where Blair was going to take this, Serena had hoped that it would be her and not Eric. "It's because of their excellent program which aids so many young addicts and alcoholics, that a student here with us today is clean and sober... at least for now. Can I please have Serena Van Der Woodsen join me on stage?" she then requested as everyone turned back to look at Serena, as all Serena could do was stare at her friend with all the hurt in her eyes that she would even take it there, but out of all the things…she was just glad that Eric could breathe a sigh of relief. Naruto could only shake his head in disappointment this petty spat needed to be resolved and soon.

"I always knew she'd be a druggie" Katy whispered to Isobel while Serena made her way through the crowd. Jumping up on the stage, Dan quickly grabbed on to Blair's arm

"Let go of me Humphrey" Blair retorted

"No" Dan replied as he nearly dragged her off stage just as Serena had grabbed the mic.

* * *

 ** _Gossip Girl: Honesty may be the best policy in some zip codes but not in this one and not this week because "I Was a Teenage Drug Addict" is not exactly a winning college essay._**

* * *

Dragging Blair into an open classroom, Dan quickly closed the door behind them as she just stood there in anger. Folding her arms, she watched him pace the floor as if he were extremely pissed with her but at this point, she could care less as to what Humphrey was feeling. It wasn't exactly how she wanted to do it, but she felt a sense of pride knowing that she finally put a bump in Serena's plan. She began to relish the look on the Brown representatives face once he had learned this information. The great Serena van der Woodsen was nothing more than a recovery addict, there was no way in hell that Brown was even going to think about Serena now that her reputation had been tarnished for all to see. Finally coming up with the words to say to Blair, Dan ran his hand through his hair just hoping that there was a soul inside of her that would comprehend the damage she had just done.

"Do you understand what you've just done?" Dan said angrily

"Yeah, I finally revealed the real Serena…and I feel good, so spare me the Full House moment Humphrey" Blair replied "I could care less what you feel about me because at the end of the day I'm not trying to impress you, I've been betrayed and I just got a little bit of an old fashion case of revenge" she said

"That's what that was? It just looked like you being a total bitch" Dan told her "You think you got back at her but you looked just as bad up there" he yelled

"That's your opinion" Blair yelled at him

"You want to know what the sad thing is, you think your so damn smart but in this….you're the idiot. You're the complete fool in this scenario" Dan told her before she slapped him across the face. Surprised by the force behind the slap, he took a moment to massage

"Look who is talking, the boy that works for my mother. The boy, who's father still thinks he's a rocker. The boy who has no clue about this world" Blair replied in the nastiest of tones at him while he still massages his face as he turned to look at her "I'm done with this, and considered yourself fired" she then added with the same coldness before she made her way over to the door

"It was Eric," Dan said causing her to stop dead in her tracks

"What?" Blair asked.

"You got the wrong person" Dan said "The van der Woodsen that was at the Ostroff Center was Eric" he said as she slowly turned around to look at him like she had seen a ghost "See that's the funny thing about revenge, you get so blinded by it that you forget to look at all the facts, because if you had asked specific questions to Dr. Bryant than you would have known that the only reason why Serena frequented the center was because she was coming to visit her brother, Eric van der Woodsen" he said before he walked past her and made his way out of the classroom.

"Dan, wait!" Blair called out as tears began to well up in her eyes at what she had done to not just her best friend but to someone at one point, she considered to be her little brother as well. Coming out into the hallway, Blair was caught off guard to see the Headmistress standing in front of Dan

"So you two put on an interesting display out there," The headmistress said.

"I can explain…" Blair replied as she tried to take responsibility

"I really don't care to hear why it was necessary to reveal that Serena van der Woodsen attended the Ostroff Rehabilitation Center, I would buy it as an honest goof but I'm in no mood to hear any reason" The headmistress said as Dan just hung his head in disbelief by today's events "You two, detention for two weeks" she told them.

* * *

 ** _Gossip Girl: Another bomb lands in Blair's lap. Will she use it as ammunition or will she finally surrender and put down her arms?_**

* * *

Holding her umbrella that shielded her from the rain that poured so frantically, she gripped on tight as she made her way through the silenced park. She had hoped that the next day she would feel some sort of victory that she had put a wrench in Serena's future, but the only thing she had learned was that maybe revenge was something she'd have to let go in order to forgive. She didn't want to hurt or feel betrayed anymore because frankly, it was something that made her feel even lesser than she was. If she was ever going to rebuild and move on then she had to realize that she would have to find it within herself to forgive. Coming up a secluded spot with regal arches, Blair was relieved to see that she still knew a bit about her friend that so she wasn't a complete stranger to her. Looking up, Serena was caught off guard to see Blair standing there before her. Closing up her umbrella, Blair slowly walked towards her friend as Serena began to rise from her seat hoping that it wouldn't be yet another smackdown between them.

"Whenever something was bothering you, I would always find you here" Blair observed of the place she had come to known ever since knowing Serena

"You here for another catfight?" Serena asked before Blair opened up her clutch purse and pulled out a white envelope before closing to hand over to Serena

"What is this?" Serena asked

"A letter. I wrote it to you while you were away at boarding school" Blair told her as Serena looked on at the envelope wondering if she should open it "I never sent it through…I figured what's the point" she said as tears began to well up in her eyes "Dear Serena, my world is falling apart and you're the only one who would understand. My father left my mother for a 31-year-old model; a male model. I feel like screaming because I don't have anyone to talk to" she cried "You're gone. My dad's gone. Nate's acting weird. Where are you? Why don't you call? Why did you leave without saying goodbye?….. You're supposed to be my best friend. I miss you so much. Love Blair" she told her

"Why didn't you send it," Serena said trying to hide her tears "I could've…" she said before Blair interrupted

"You could've what?…you knew Serena, you didn't even call" Blair cried

"I didn't know what to say to you. I didn't know how to be your friend after what I did" Serena cried "I'm so sorry" she told her friend

"Humphrey gave me a rude awakening about Eric. I guess your family has been going through a hard time too" Blair said as she started up a conversation.

"I thought you and Dan don't talk," Serena said through muffled tears that she wiped away.

"We don't" Blair laughed. With that, the Queen bee left as Serena was still crying and Naruto decided to hug her as he saw what was going on.

* * *

Taking a rag, Dan began to clean the kitchen counters while Darota finished preparing lunch for the day. He hadn't really argued or tried to go behind Blair's back to see if she had grounds to fire him because he was just at this point where he was tired of dealing with Blair in general. Throwing the rag over his shoulder he began to wonder if he should tell Darota that this was his last day on the job. Maybe this was for the best he thought to himself because with the added detention that they would have to serve together, there was only so much Blair Waldorf he could take. Putting the dishrag in the sink, Dan nodded over at Darota before he made his way out of the kitchen with a slight laugh on his face. Grabbing his jacket that was resting on the chair, he began to put it on just as the elevator doors opened. Looking over at the elevator he soon wished that he had hurried up so that he would have avoided seeing Blair.

"I'm leaving," Dan said as he attempted to walk past her but she had cut him off.

"Actually, do you think you could stay?" Blair asked.

"No," Dan said as he attempted to leave again but she had once again stepped in front of him.

"But I think you should stay," Blair said.

"I don't want to" Dan replied as he slid over to move past her but she got in front of him.

"I'm trying here," Blair said.

"This is you trying to do what?" Dan asked in confusion as to what cutting him off at every step was supposed to translate to.

"To you know, do that thing when you were wrong about something," Blair said not eagerly wanting to admit that she was wrong.

"You mean to apologize," Dan said.

"Yeah, that thing" Blair replied

"I'll be waiting for that to happen," Dan said before he tried to move past her but yet again she cut him off "Waldorf!" he said in frustration

"Look, I can't do that because I…I can't stand you," Blair said before he cut her off

"And this is an apology. You need help, serious psychiatric help" Dan told her

"I'm trying Humphrey," Blair said through gritted teeth "You can't stand me. I can't stand you. So why don't we just admit that and move on from this" she said

"So is this a momentary thing due to guilt and ignorance of facts or is this something that's going to stick?" Dan asked

"Me disliking you is pretty much set in stone" Blair replied "But I think I can dislike you while you still work here" she compromised

"So what? Your untiring me now?" Dan asked

"Yes, I'm unfiring you," Blair said

"Is this the closest I'm ever going to get to an apology?" Dan asked

"This is the closest your going to get to me" Blair replied

"Fair enough," Dan said as he turned to take off his jacket

"Humphrey" Blair said as he turned to look at her "You tried, yesterday…you tried to warn me and then stop me. Why not let me go through with it not knowing the repercussions?" she asked

"Because, Waldorf, I don't think you're that heartless as you proclaim to be" Dan smirked before he headed back into the kitchen.

* * *

 ** _Gossip Girl: So what will it be? Truce or consequences? We all know two wrong people, don't make a right relationship. What happens next? Only time will tell. XOXO Gossip Girl._**

* * *

 ** _Author notes_**

 ** _Yeah I know there wasn't too much Naruto in here and im sorry for that fr fr, But request of what pairing it should be rn Serena does like Dan and they're sort of a love triangle but once i get deep into the story that shape will only consist of one pairing._**


End file.
